


The Hunter Groom

by A_Zap



Category: Supernatural
Genre: Adventure, As you wish, Comedy, Destiel - Freeform, Humor, Love, M/M, Parody, Princess Bride, Princess Bride AU, Romance
Language: English
Status: Completed
Published: 2015-09-02
Updated: 2015-11-07
Packaged: 2019-02-14 03:41:24
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 20
Words: 30,099
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12999087
Author URL: https://archiveofourown.org/users/A_Zap/pseuds/A_Zap
Summary: Love, Adventure, Danger, Romance. Jimmy tells his daughter Claire the tale of The Hunter Groom. Dean loses his true love Castiel, but years later his life is turned upside down as the hunter becomes engaged to the princess of the Kingdom of Heaven. What's next?Destiel in The Princess Bride AU.





	1. The Story Begins

Claire let out an irritated huff, and let her phone fall out of her fingers. She was so bored; being sick sucked. Not even her phone could entertain her anymore and she wasn't allowed to have a TV in her room to try to distract her.

She fell back against her pillows and pursed her lips. Silently, she wished that there was something, she didn't care what, to take a way the boredom.

There was a small knock on her door. For a moment, she thought that her prayers had been answered as she called out, "Come in."

Then it was just her dad, Jimmy, walking in.

"Hey, Dad," she rolled her eyes. He was such a worrywart.

"Hey, Claire. Feeling any better?" Jimmy made his way over to her bed, and gently laid his hand on her forehead to check her relative temperature.

"Fine." Claire pushed his hand off. "Just bored out of my mind." She shot him a pleading look that she hoped would convince him to give her a TV.

Jimmy smirked. "Good thing I brought something for that." He held up a book.

She scoffed. "A book? Really?" Claire crossed her arms. "How about no?"

"I thought I'd actually read it aloud to you." Jimmy pulled up a chair next to her bed.

She stared. "I'm almost eighteen, Dad. I don't need a bedtime story."

"This is special though. You know my one set of cousins that… well, there are a lot of them?" She nodded. "This was written by one of them about one of the others."

"Ooo! Who?" Claire was suddenly into it, and she leaned over to see the cover. Then she flipped through the first couple of pages to check names. She smiled. "A book by my fun uncle about my favorite uncle, huh?"

"Technically, they're cousins." Jimmy corrected. "Still, this is an adventure story."

Claire thought it over for a moment. It was either this or boredom.

"Read on." She said with a wave of her hand.

Jimmy cleared his throat. "The Hunter Groom." He announced the title as he turned to the first page.

* * *

Once upon a time…

* * *

"Wait, I thought this was an adventure story. It sounds like a fairy tale." Claire frowned. She was definitely too old for those.

"It's a fantasy-adventure romance." Jimmy frowned right back. "Are you going to let me read or not?"

Claire sighed and Jimmy took that as a sign to continue.

* * *

Once upon a time, in a place known as the Kingdom of Heaven, there lived a young man by the name of Dean.

He was raised in a small village, and he followed in his father's footsteps by becoming one of the best hunters there. He was celebrated and beloved for his catches were often a boon for the poor village. Even after his father died in a tragic accident while he was still young, he was never lonely and found himself content with his work and life.

One of his favorite activities was messing with another young man in the town. This man worked mostly at the stables but he had a gift with creatures so he often helped with any animal that was hurt or in trouble. Dean met him one day when the man was out in the forest scoping out a bee colony. This young man's name was Castiel.

Dean loved ordering Castiel around. Some of the orders were ludicrous or seemed impossible and Dean waited for the day when the stable boy would snap and finally fight back or protest.

However, each time, Castiel would just give Dean a look that felt like it was going all the way to his soul. Then he would say, "As you wish." Castiel would go off and do whatever Dean had asked, no matter how long it took. When the task was done, he would always return to Dean to tell him that it had been done.

Eventually, Dean realized that when the young man said, "As you wish," what he was really saying was, "I love you." For a while, he just continued as things were, unsure of what to do with this. Then he realized one day that he returned the feeling.

One panic attack in the privacy of his cabin later, Dean even accepted his feelings.

The two began a relationship, and they were both happy. Still, it was not to last as war broke out between Heaven and its close neighbor, the Kingdom of Hell. Several men were conscripted into the army and forced to be soldiers. Castiel was one of the people chosen to serve.

"Come on, Cas." Dean begged Castiel as he packed up his things. "We can run away and avoid all of this."

"I have to Dean." Castiel replied, putting the finishing touches on his pack. "It is my duty to serve this country, and…" He walked right into Dean's personal space. "I wish to protect you."

It was hard for Dean because he felt like he was losing the one of the only people who cared for him. He couldn't bring himself to look the other man in the eye.

"I will return." Castiel promised, catching the bottom of Dean's chin as he looked downward and bringing his eyes up to meet his own. "We share a profound bond, and no one can break that. Not some war, not any distance, not even Death." He smiled that tiny smile that made Dean's heart pound. "This is not something that happens every once in a while or even a century. We have true love, and no one can stop that."

With a final kiss, Castiel left. Dean watched him go with a heavy heart, though he tried to believe in his love's words.

It was months later, after peace had returned and Dean eagerly awaited the return of his lover, when the news came. While returning to Heaven, the ship carrying Castiel home was attacked by the infamous pirate, the Avenging Angel. Dean despaired because everyone knew that the Angel took no prisoners.

Castiel was gone.

For a week, Dean shut himself away, consumed by his grief.

"I shall never love again." He vowed.

Five years passed, and that is where the story truly begins.


	2. Kidnapped!

A lot had changed in the five years since Castiel's death. The King of Heaven had disappeared, and in his place, his son Michael led the people for the moment, though he had yet to take the throne. That, however, was not the talk of the kingdom.

The princess, Anael or Anna for short, had decided to take a groom. According to the laws of that land, the oldest could not take the throne unless one of the royal children was married, so Anna had decided to marry the hunter, Dean, who by that time had become famous throughout the kingdom for his unrivaled skills.

Dean did not love Anna. He respected her right to choose anyone for a spouse though, and he couldn't exactly turn down the princess. He consoled himself with the thought that at least she was very attractive.

"You'll love me one day." Anna would reassure him with a smile. Luckily for him, she didn't take offense when Dean snorted.

He knew that he could never love her though. He had already made that mistake, and since then he had hardened his heart. Anna wasn't going to get to him.

Being in the palace made Dean unhappy; he preferred the tranquility and comfort of the forests. Everyday, the hunter would ride for hours on his beloved horse, Impala, who was the only other being he truly loved. As the wedding day got closer and closer, Dean spent more and more time outside with Impala.

It was as he was riding through the forest a few weeks before the wedding that he came across a group that waved him down. As he slowed, Dean studied the motley crew.

There were three of them. Two of them were fairly short, while the third was a giant. One of the short ones wore a black suit, which wasn't what most people wore, and had thinning black hair. His lips were curled into a scheming smile. Dean had seen that smile enough to know that this man was probably not to be trusted. He was not obviously armed, but the hunter knew better than to assume.

The next one was only slightly taller than the first. His blonde hair curled down, bangs flopping down to frame amber eyes. His eyes held a mischievous glint, but his hand on the hilt on the blade at his side was familiar and easy. He obviously knew how to use the sword. He also appeared to be sucking on a candy as he smirked at Dean.

The giant had long brown hair that reminded Dean of a woman. He had intelligent, hazel eyes that were trained on Dean. He had an odd knife strapped to his thigh, and a pistol on his belt. He looked somewhat uncomfortable and stood with his arms crossed over his broad chest. Just from his height and weight alone, Dean did not want to tussle with him.

Dean had a bad feeling about this.

"Can I help you?" Dean asked, skepticism coating his voice as he raised an eyebrow at the crew.

"Yes." The shortest guy replied, his British accent now obvious. "We are but humble circus performers: myself, Crowley, and Gabriel and Sam here." He gestured to himself and the other two. Dean smelled a rat, even as Crowley turned to crack a salesman smile at him. "Is there a town nearby where we might earn some money?"

"No. There's nothing for miles." Dean said, tensing up.

Crowley's smile became shark-like. "Then, there will be no one to hear you scream."

Gabriel and Sam came up towards him in a threatening manner.

"Like hell." Dean kicked out and caught Sam in the shoulder.

He winced a bit but he easily dragged Dean off of Impala.

"Hey, watch my baby!" Dean punched out at him. Sam grunted a bit, and punched back but Dean dodged.

He had spent his whole life hunting, so he knew how to hold his own in a fight. This Sam though was just as good and kept up with him punch for punch.

"Not bad." Dean grinned as he landed a kick right in Sam's stomach. He stumbled away, as Dean finished speaking the thought, "But I'm better."

"Not better than me." An impish voice came from behind Dean. Before he could turn around, there was a dull pain in his skull and he collapsed into unconsciousness.

Sam caught Dean as he fell, and in front of him, Gabriel lowered his arm from where he had hit Dean with the hilt of his sword.

"Well," Gabriel said as he sheathed his sword, "that was easy."

"Speak for yourself." Sam grumbled as he picked up the hunter.

"Ah, come on." The swordsman nudged the giant. "You know you love it."

"Boys," Crowley said disdainfully as he picked some lint off of his suit, "time is money, you know. And we are on a schedule."

"Right, boss." The two muttered, as they made their way towards their getaway boat. Gabriel grabbed the reins of the horse and led it behind them.

"Now, put the pretty prince on the ship, and get ready to launch." Crowley took the reins from Gabriel and pulled out a scrap of cloth. On it, there was the visible crest of Hell.

"What are you doing?" Gabriel leaned against the side of the ship, having done all of the preparations that needed to be done.

"This shows the crest of the royal family of the Kingdom of Hell. It's from one of the uniforms of their army officials." Crowley finished placing it, and slapped Impala's rear. The horse bucked and then ran off back in the direction of the castle.

"That doesn't really explain what you're doing." Gabriel said dryly.

"Well, Hell is the sworn enemy of Heaven." Sam commented while making sure their prisoner was relatively comfortable.

Crowley sauntered over to the boat and climbed in. "Once the horse reaches the castle, the fabric will make the prince suspect that the Hellions have abducted his precious sister's lover. When they then find his body in Hell's territory, his suspicions will be confirmed." He smirked.

Sam jerked up at his words. "You never said anything about killing anyone." He growled, a scowl crossing his face.

Crowley sighed. His entire countenance was that of an adult explaining things to a child. "I've hired you to help me start a war." He sniffed and straightened his suit. "It's a prestigious line of work, with a long and glorious tradition."

Sam was still frowning. "I still don't think it's right to kill an innocent man."

"Well, good thing I didn't hire you to think." Crowley threw back.

"I kind of agree with Sammy." Gabriel popped another candy into his mouth. "If he deserved it, then I'd be all for it, but under the circumstances…"

"Enough!" Crowley chopped his hand in front of him, silencing their protests. He turned to Gabriel. "What happens to him is none of your concern. I will kill him. And remember, when I found you, you were so broke, you couldn't even buy a piece of bubblegum. As for you," he rounded on Sam, "do you really want me to send you back where I found you? Unemployed in Greenland? Because that would bring you oh so closer to your dream of going to school."

Neither of his employees could meet his eyes.

"Now, set sail and let's finish this job." Crowley went to go check the prisoner himself.

Gabriel went to man the rudder as Sam unfurled the sail. The giant looked up and saw Gabriel's annoyed expression. He decided to cheer the swordsman up a bit.

"You know Crowley, he can… fuss." He said.

Gabriel's face lit up. "I think he just likes to scream at us." He replied cheekily.

"He probably means no… harm." Sam lead.

"He's really very short on charm." The two of them snickered at that. Gabriel gave a sigh and smiled at giant. "Ah, Sam, you know how to make me smile."

"Well, we have known each other for quite a while." Sam replied with a smirk. They laughed again.

"Shut up! I'm not paying you to tell jokes!" Crowley snapped.

"Yeah, instead we just carry the yoke." Gabriel muttered to Sam.

The giant chuckled and raised his hand to shade his eyes as he looked ahead. Finally, the ship was moving forward. "Gabriel, are there rocks ahead?"

"If there are, then we'll be dead!" Gabriel laughed.

"Agh!" Crowley yelled bracing his hand against his head. He couldn't help but wonder why he hired these two morons in the first place. Unfortunately, he was stuck with them now.


	3. No Swimming Zone

The sun had already set by the time Dean woke up. He jumped a bit as he regained consciousness as he hadn't expected to wake up somewhere besides his bedroom. Still, the memories that had led to him being on a boat in the middle of nowhere began to trickle in.

Dean swore under his breath as he looked at the men who had kidnapped him. Crowley noticed his observations.

"Well, Sleeping Beauty is awake." He drawled.

"Where the hell am I?" Dean demanded.

Crowley raised an eyebrow. "I would have thought that even you would notice that we're on a boat."

"I get that." Dean huffed. "But where are we going?"

"You'll see soon enough." The Brit walked towards the bow.

Sam frowned and leaned towards Gabriel. "Kind of a drama queen, isn't he?"

Gabriel snickered. "Yeah." He looked behind them and frowned before turning forward again.

"Well, thanks so much for the explanation." Dean said sarcastically and he shifted to lean more comfortably against the boat's side. He knew that he would have to wait for the perfect moment to make his escape.

"Hmm. We should reach the cliffs by morning." Crowley gazed before them, and then he caught Gabriel once more twisting around in the corner of his eye. He turned to the swordsman. "Why are you doing that?"

Gabriel looked at the short man. "I'm making sure no one is following us."

Crowley snorted. "That would be inconceivable." He waved Gabriel's concerns away.

"Do you really think you can get away with this?" Dean asked, completely serious. "Michael may be a dick, but he really does care about his sister. He'll catch you," he leaned forward a bit, "and you will be hanged."

Gabriel and Sam exchanged worried looks, but Crowley didn't even blink. "I think you should worry about yourself first." He saw Gabriel looking back again. "And will you stop that! It's almost over, so stop worrying."

"Are you sure nobody's following us?" Gabriel didn't sound laid back for once.

"It would be absolutely inconceivable. No one in Hell knows what we've done, and no one in Heaven would be able to come after us so quickly." Crowley explained. He frowned as Gabriel glanced back again. "Out of curiosity, why do you ask?"

"Oh, it's nothing." Gabriel shrugged and jerked his thumb towards the water behind him. "It's just I looked back and it seems like there's someone following us."

"What?" Crowley and Sam hurried over to stand next to Gabriel, and they stared in shock.

Sure enough, within visible distance, there was a sailboat following after them. It flew no colors nor had any distinctive markings, so there was no way to see whom it belonged to.

"It must be some sort of fisherman doing some night fishing… in dark, monster-infested waters." Crowley weakly tried to reason.

As the three looked behind the boat, Dean saw his opportunity. In a swift movement, he stood and leaped over the side of the ship.

The splash caused the three kidnappers to whirl towards where Dean had been moments before.

"The fool!" Crowley cursed the hunter under his breath. Upon seeing neither of his employees move, he snarled. "What are you doing? Get in after him."

Gabriel gave him an incredulous look. "I go to the beach to pick up hot people, not swim."

The Brit switched his glare to the giant. "I only doggy paddle." Sam said, as he mimed the stroke.

Crowley growled. "After him! To the left!" The two employees jumped to and quickly got to work.

Meanwhile, Dean felt he was making decent time. He didn't know how far away the shore was, or even if he was going in the right direction, but he figured it was better than staying with those crazies. He continued to swim until he felt something brush against his leg.

Dean stopped, confused. Immediately, a shrieking noise filled that air. He turned, the noise making him nervous.

Across the water, he heard Crowley chuckling. "Know what that sound is?" He paused dramatically. "Those are Leviathan. And their favorite food is human flesh."

Dean felt something brush his leg again as he tread in the water. In the moonlight, he could now make out dark, large, snake-like shapes swimming around him.

"If you swim back now, I can guarantee that no harm will come to you." Crowley didn't sound that bothered now. "You won't get an offer like that from them."

* * *

"What's with that look?" Jimmy asked as he looked up from the book.

Claire blinked. "What?"

"You look kind of worried." Jimmy tried to hide a grin. "Are you actually getting into this?"

She shifted a bit, somewhat uncomfortable. "It's more just imagining them doing stuff like this. It's funny."

"But you look worried."

Claire gave an offended sniff, and punched Jimmy lightly in the arm. "Just get back to reading."

Jimmy let his smile show and turned back to the story. "Okay."

* * *

Dean gritted his teeth. Surely, these things couldn't be that bad. He really didn't want to listen to that smug bastard.

A giant shriek came from in front, and he jerked back as an enormous mouth filled with rows of teeth appeared. He yelled in fright.

Before those teeth could clamp down on him, he felt a hand grab the back of his shirt and yank him from the water.

Dean sputtered for a moment, disorientated by the sudden change in scenery, but he quickly realized what had happened. Sam held him up and gave him a pitiful look.

"Get him in here!" Crowley ordered. "Now put him down!"

With Gabriel's help to maneuver him, Sam dumped the hunter onto the deck. Dean stood there shivering and glaring at his captives, even though they had technically just saved his life. He brushed his hair back.

"Learned your lesson?" Crowley smirked. He leaned into Dean's space. "I suppose you think you're brave?"

"Only compared to some." Dean replied.

"Tell me that when you aren't walking around in wet socks." Crowley countered.

Dean didn't deign to answer him and instead went to sulk back where he had first been. Satisfied, Crowley returned to the bow.

Gabriel glanced between the two. "Great, another drama queen." He muttered as he went back to his place at the rudder.

Sam sighed and wished that this whole debacle were over.

"Uh, that guy is getting closer." Gabriel admitted.

"He's not going to be a problem! Just keep sailing!" Crowley didn't even look back at him. Gabriel made a face at his back, but didn't say anything.

Silence fell over the ship as the sun eventually rose. It illuminated their destination.

Unfortunately, it also made their pursuer much easier to see.

"Look! He's practically on top of us." Gabriel looked at their sail speculatively. "I wonder if he's using the same wind as us."

"It doesn't matter. See?" Crowley pointed at the towering sheets of rock before them. "The Cliffs of Insanity! Now, move it!" He turned to glare his employees into movement. They scrambled to bring the boat in and dock.

"Now, then." The man made his way over to Dean.

Dean stood and fell into a fighting stance. He wasn't sure what was going to happen next, but he was not going to let himself be taken so easily again. He wasn't some freaking damsel in distress!

Crowley noticed this, and gave a deep sigh. "Moose." He called.

Sam also sighed. "Sorry about this." He said as he easily dodged Dean's punch and kick to get behind him and hold him still. The hunter struggled, but the giant was a lot stronger than him.

Crowley enclosed a pair of handcuffs onto Dean's hand and feet. After all, it wouldn't do for his prize to run away.

"All right then." Crowley clapped his hands together, and a smirk crossed his face. "It's time to climb."

Sam put on his harness, and the three others got into place. The giant grasped the rope hanging down from earlier preparations and began to climb.

"Only Sam is strong enough to climb up these cliffs. That guy can sail around all day, and he'll never catch us." The Brit said almost gleefully.

Unknown to him, a pair of blue eyes was watching and studying the group making its way up the cliffs. They were calculating, as they never left them, and filled with intelligence.

Slowly, a small smirk formed under those eyes.

**Notes for the Chapter:**

> AN: In regards to this story, when I started drawing parallels between the two universes, I immediately thought that Leviathans would be great for the Shrieking Eels. After all, they scream, love water, and have giant, multiple rows of teeth. This story is a lot of fun in that way.


	4. Climbing Insanity

The four slowly made their way up the rope. Dean was bored, as one could only look at stone cliff faces for so long.

"Uh," Gabriel said, looking down. "That guy's climbing the rope. And he's gaining on us." He paused as his brows furrowed. "He's also the most suspicious person I've ever seen."

"What?" Crowley followed his gaze. "Inconceivable."

Dean glanced down. There was a man climbing up the rope. He had dark hair that was tousled from the wind, and he was also wearing a mask over his face.

And a trench coat.

"Did he think that the trench coat wasn't suspicious enough so he just had to wear a mask as well?" Crowley muttered in disgust. He glared at Sam. "Faster!"

With a grunt, Sam picked up his pace. However, with another look down, Dean could see that the guy in the trench coat was still gaining.

"Faster!" Crowley growled.

"I thought I was going faster." Sam snapped back as he tried to go a bit faster, but the strain was easily seen in his bulging muscles.

"You're supposed to be some sort of colossus, a great legend!" Crowley was obviously losing his patience as frustration filled his voice. "And yet he gains!"

"Well, I'm carrying three people." Sam sounded annoyed even as he grunted once more from his efforts. "He's just got himself."

"Next time I need a giant, I'm going to be getting a different one." Crowley muttered.

"Well, how would you like to do this then?" Sam asked, throwing a bitch face. "Or, better yet, how about I lose some of the weight I'm carrying?" He momentarily looked down at where Crowley was hanging.

The Brit huffed, but remained silent. After all, even he knew when not to push Sam.

Still, as Dean watched, the mystery man continued to gain.

It didn't really matter though as they managed to reach the top of the Cliffs of Insanity. Sam hung from the rope as Gabriel slipped out and helped Crowley and Dean onto safe ground within the ruins of a castle. Once all of his passengers were off of him, Sam pulled himself up over the edge. He stretched his sore muscles as Gabriel watched the mysterious man draw nearer. Dean rolled his eyes at both of them.

Crowley made his way to the rock that anchored the rope. Pulling out a long knife from the small of his back, he began to saw at the rope.

"What are you going now?" Sam asked, exasperated.

"Getting rid of that pesky insect." With a final snap, the rope broke and fell over the cliff. Gabriel and Sam looked down over the edge. Dean inched over to join them, and lifted an impressed eyebrow at what he saw.

The man was still hanging there, clutching onto the rocks of the cliff face.

Gabriel and Sam also looked suitably impressed. "Nice arms." Sam commented.

Crowley joined them. "He didn't fall! Inconceivable!"

"You know, you're smart and all," Gabriel frowned at him, "but you keep using that word. I don't think it means what you think it means."

"I think the word you're actually looking for is impossible." Sam suggested. He checked over the edge again and his eyes widened. "Holy crap! He's climbing."

The others looked over to confirm Sam's observation. It was true. Slowly but surely, the man was feeling out handholds and making his way up.

Crowley growled at the sight, annoyed. He clenched his fist for a moment, and Dean could see it trembling. Then, he somehow became completely calm, and even smiled a bit. "Whoever he is, he's obviously seen the princess – "

"Excuse me?" Dean asked, taken aback.

"Sorry, the prince." Crowley rolled his eyes. "And he must therefore die." He pointed at Sam. "Carry him. We'll be heading straight for Hell's plains. You." He turned to Gabriel as Sam picked up a protesting Dean. "Catch up when he's dead. I don't care if he falls or you use your sword; I want him dead."

"Hmm." Gabriel popped another candy into his mouth. "You know, I think I'm going to duel him left-handed."

"You know what a hurry we're in!" Crowley hissed. "There's no time to play."

"There's always time to play." Gabriel asserted. "Besides, it's the only way I'd be satisfied. If I used my right, it'd be over way too quickly."

"Fine." Crowley facepalmed. "Have it your way. I don't care as long as it gets done." He walked away from the cliffs.

Sam shifted Dean's weight on his shoulder. The hunter continued to try kicking him. "Be careful." He warned Gabriel. "After all, you can't trust men in masks or trench coats, so he's double trouble."

"I'll be fine." Gabriel assured him. "And once I win, will you give me a smooch?"

Sam's cheeks turned a bit pink. Before he could answer, Crowley bellowed, "I'm waiting!"

The giant looked at their boss. "Not the time, Gabriel. See you later!" He hurried off.

Gabriel sent a cheeky grin after him and waved.

This was going to be one fight he had to win.

**Notes for the Chapter:**

> AN: Really short chapter, but it was getting way too long so I split it into two chapters. Tune in next time for swordfighting!


	5. The Swordsman's Challenge

"Ah!" Gabriel stretched his arms upward. The swordsman gave a few other stretches to prepare himself for the upcoming duel. He glanced at the edge, but frowned as the man was not there yet.

He decided a greeting was in order. "Hello there!" He waved as the man in the mask looked up at him. "Slow going?"

The man seemed unimpressed. "I beg your pardon." Gabriel jumped a bit at the guy's voice. It was deep and sounded like he had been gargling gravel. "This is not as easy as it may look, so I'd appreciate it if you would not distract me."

"Sorry." Gabriel said, surprised to feel a bit sheepish.

"Thank you." The man returned to his climbing.

Gabriel sighed and turned away from the cliff. He drew his blade and did a few practice steps. His sword dropped. He was so bored.

Gabriel hated being bored.

He sheathed his blade and walked back over to the edge. "Uh," he waited for the man to look up again, "you don't think you could hurry it up a bit?"

The man in the trench coat grunted as he struggled to keep his grip on his latest handhold. "Look," he said impatiently, "if you're in such a hurry, you could lower a rope or tree branch or something that's useful in general."

Gabriel blinked. That hadn't actually occurred to him. "I could do that." He turned to where there was still quite a bit of rope wrapped around the anchor rock. There was probably enough to reach the man. "I've got some rope here, but I don't think you would accept my help." He called down to him. "Since I'm only waiting around to kill you and everything."

The man sighed as he climbed a bit higher. "That is not a very good way to start a relationship."

Gabriel chuckled a bit. "I don't know. My ex-girlfriend and I started out when she tried to kill me." He frowned. "Actually, that's also how our relationship ended, too."

"As fascinating as that is, could I just get back to climbing without being bothered?" The man asked. Gabriel could feel his glare from here.

"Well, if I lower the rope, I promise that I will not kill you until you get to the top."

The man did a tricky hop to grab onto the next ledge. "You may find that comforting, but I don't. You'll simply have to wait."

Gabriel scrunched his nose. "I hate waiting." He whined; he hated waiting almost as much as he hated being bored. He turned away, and thought about it a moment. There had to be some way to convince him. The swordsman walked back to the edge. "I could swear on my candy?"

The man snorted. "Considering that you are eating it and steadily lowering your supply, that's not reassuring."

"Is there any way that you will trust me?"

"I can't really think of anything."

Gabriel paused as something came to mind, but it would be big. He took a deep breath and seriously said, "I swear, on the soul of my father Charles Shurley, you will reach the top alive."

The man looked at him for a long moment, and it was like his very soul was being gazed at. Finally, the man replied, "Throw me the rope."

Gabriel uncoiled some of the rope and threw it down to him. After that, it didn't take the man long to make it to the top.

"Thank you." He was breathing a bit hard, but he straightened up and began to draw his sword.

"Wait a sec. We can start when you're ready." Gabriel held up a hand to indicate he should slow down.

The man continued his somewhat creepy staring. Had he even blinked at all? "Thank you again." He sat down on one of the nearby rocks. Gabriel flopped down across him. He watched as the stranger took off his boot and flipped it upside down, shaking it. Several large rocks fell out.

Gabriel lifted his eyebrows. That was a surprise. It occurred to him suddenly that he should do his finger check. "Excuse me," the man looked up with his own eyebrows raised, "you don't happen to have six fingers on your right hand, do you?"

The man in the trench coat gave him a confused look and tilted his head. "Do you always start conversations this way?" Still, he held up his right hand to show off his five fingers.

Gabriel huffed. He really should have expected this. "My father was killed by a six-fingered man. Though I do not blame him, for he was simply a henchman. It's his boss, some sort of ugly deformed hobbit that I really want. The minion is simply the best way to find him." He threw another candy into his mouth as he leaned forward towards the man. "You see, my father was a great sword maker. The six-fingered man and his boss showed up, and the hobbit requested a special sword. My father decided to take the job."

Gabriel drew his sword and gave it a melancholy smile. "It took him an entire year but eventually he finished." Flipping it over, he held it out to the man in the trench coat hilt first. Considering the guy also had a sword at his side, he thought he might be able to appreciate it.

The man quickly finished putting his boot back on and took the blade. He studied it, his eyes drinking in everything. Admiration bloomed in his gaze. "I've never seen its equal." He handed it back.

Gabriel grunted. "Yeah, it's a real masterpiece. When the two returned and the boss demanded it, he said he would only pay one-tenth of the promised price. My father, of course, refused. With a single order, the six-fingered man cut down my father." He bitterly sheathed his sword. "I loved my dad, and it just figures that one of the few times he decides to be assertive, he gets killed. Anyway, I naturally decided to challenge the murderer to a duel."

"The murderer, as in the six-fingered man?" The man asked.

"That's who I blamed at first, so yes." Gabriel replied. "The boss left after ordering him to kill me too." He shrugged. "I failed, of course. But the six-fingered man didn't kill me. He left me with this," he fingered a pale scar at the base of his neck, "and a heartfelt apology for the death of my father."

"Leading you to blame the man who ordered the death." The man concluded. "How old were you?" He tilted his head again as his face scrunched up.

"I was eleven years old." Gabriel stood and stretched. "Once I recovered, I then devoted my life to the study of swordplay, so I won't fail next time. That way, when I find that deformed hobbit, I can look him in the eye and say, 'Hello. My name is Gabriel Shurley. You killed my father. Prepare to die.'" He grinned at the thought of getting his revenge.

The man in the trench coat looked impressed. "You have done nothing but study swordplay? I cannot help but admire your dedication."

"Well," Gabriel said a bit sheepishly as he rustled his hair a bit, "it's been more of a pursuit than a study lately. I haven't been able to find him, and it's been twenty years. I'm working for Crowley in order to pay the bills. It turns out that there isn't much money in revenge."

"I see." The man rose and drew his blade. "I certainly hope you find the two someday."

"You're ready?" Gabriel felt his mood pick up from melancholy land. After all, they were going to fight!

The man shrugged and held the blade loosely in his left hand. "Whether I am or not, you've been more than fair."

Gabriel grinned as he drew his sword. "You seem a decent fellow." He held it up at the ready. "I hate to kill you."

The man in the trench coat held his own sword up. "You seem a decent fellow." Lightning seemed to crackle in his eyes. "I hate to die."

Gabriel took a deep breath. "Begin."

The first few strokes were tentative as both of them were testing the waters. However, the blows became faster and faster as they circled and learned each other's style. They went back and forth, exchanging blow after blow.

Slowly, Gabriel began to make the man back up, forcing him to begin moving up the rocky hill.

"You are using Bonetti's defense against me, huh?" The swordsman kept an eye on his opponent as he identified the man's moves.

The man in the trench coat managed to give a small shrug as he continued to fight. "I thought it fitting, considering the rocky terrain." He got to the top of the small slope.

Gabriel hurried after him. "Naturally, you must expect me to attack with Capo Ferro."

The two continued to exchange strikes on what appeared to have been a landing at some point. "Naturally, but I find that Thibault counters Capo Ferro, don't you?" He jumped back off the landing to avoid Gabriel's blade, standing once more on the flat ground.

"Unless the enemy has studied Agrippa." Gabriel took a running start and leaped off the landing, flipping in mid-air. He landed behind the man in the mask, who turned to meet him. "Which I, of course, have."

They threw themselves back into the fray. A smile grew on Gabriel's face as the clang of swords meeting continued to ring in the air. "You are wonderful." He admitted.

"Thank you. I've worked hard to become so." The man in the trench coat nodded at the compliment.

"I admit it: you're better than me." Gabriel's smile didn't dim a bit.

The man tilted his head in confusion. "Then why are you smiling?" He was forcing Gabriel closer to the edge of the cliff.

"Because I know something you don't."

"And what is that?"

Gabriel laughed. "I am not left-handed!" With a small toss, he switched his blade to his other hand.

He quickly turned the tables. The two of them began to make their way their way up the stairs. It was a lot easier for the swordsman to fight now that he was using his dominant hand. To his surprise though, the other man was still able to keep up with him.

The reached the top of the stairs at the balcony. Gabriel managed to direct the man towards the edge.

"You are amazing." The man in the mask said, returning the compliment.

"I should hope so." Gabriel began making the man back up. "I studied for 20 years after all." The man was pressed against the wall. Slowly, his weight began knocking the old, loose tiles off. Fairly soon, the man himself would be tipped over the edge. Their blades trembled as they were locked together.

However, there was something in the guy's eyes that made Gabriel wary. "I have something I should tell you."

"Tell me." The swordsman was game to hear what he wanted to say.

The man smirked. "I'm not left-handed either." With a push, Gabriel was forced back. The man in the trench coat straightened and switched hands. With a flourish of his blade, he came at the swordsman, and the fight resumed.

Gabriel grit his teeth. Now they were right back where they started. He started a bit as the man managed to disarm him. He watched in shock as his sword flew into the air and eventually managed to get stuck in the ground on the ground floor.

He glanced over but the man didn't come closer. The swordsman used the opportunity to leap off the balcony and use a convenient bar to swing himself over to his sword. He quickly turned around in a fighting position.

The man just smirked though and tossed his sword. It landed hilt up in a patch of grass. Then, he leapt off the balcony, swung around twice on the bar, and finally did a full flip onto the ground right next to his sword. He easily plucked it from the soil and held it again at the ready.

Gabriel could only stare in shock. "Who are you?"

"No one of consequence." The man in the trench coat said in all seriousness.

"I must know." After all, in the years since encountering the man who killed his father, he had never met someone who was even his equal at swords.

"You should get used to disappointment." The man fell into more of a fighting stance.

Gabriel shrugged. "Okay." He knew when not to push someone. He stepped forward and their blades clashed once more.

Forwards and backwards, to the left and to the right, the two of them continued to fight. They went up on rocks and the ruins of the castle. However, neither one could best the other.

Finally, they ended up in what had once been the entrance to the building. It only took a second, even as time seemed to slow down. The whirling of the blade distracted Gabriel, and his sword was knocked from his hand.

He was shocked. The swordsman couldn't remember the last time he had been truly beaten. He kneeled as the man in the mask stepped closer, blade raised. "Kill me quickly." He asked.

The man stepped out of his vision as he went behind him, but he briefly saw the frown on his face. "That would be quite a great waste. I have no wish to truly harm you; however, I cannot have you following me."

The man hit Gabriel in the head with the hilt of his sword. As he slumped to the ground, Gabriel couldn't help but moan, "Oh, the irony…"

The man in the trench coat sheathed his blade, and bent down to make sure that Gabriel was knocked out. "Please understand that I hold you in the highest respect." He said, as he gave the swordsman an awkward pat on the head.

That done, he straightened and quickly made his way in the direction that Crowley and Sam had taken Dean.

He had a mission to complete.

**Notes for the Chapter:**

> AN: So to make up for the last chapter, this one is really long. I think it might actually be the longest, though I'll admit I haven't checked. It's just that this is a really long scene, and I wanted to do it justice as it's really awesome in the original. I actually brought the fight scene up on YouTube and went step by step writing it so it could be as close as possible. Though I'll admit, Gabriel Shurley doesn't have the same ring as Inigo Montoya.


	6. Facing the Giant

"Hey." Sam was looking back towards the ruins.

"What?" Crowley snapped. He glanced over at him. "And what are you doing just lollygagging around? I am not paying you to admire the scenery."

"Well," Sam adjusted Dean on his shoulder to avoid a particularly vicious kick, "you know how we left Gabriel behind to take care of our pursuer?"

"Oh, good. He's done?" The Brit continued walking. "Now we can get our job done without any worries."

"Yeah, it's not Gabriel following us." Sam squinted to try to get a better look. "Unless he somehow grew taller and stole the guy's trench coat." He paused. "I like to think he has better taste than that."

"What?" Crowley turned around and looked behind them.

Sure enough, making his way over hill and dale, the man in the trench coat grew closer with each step. His coat flared out behind him, making it even more dramatic looking.

"Inconceivable!" Crowley growled. "He bested that moronic swordsman."

Sam shot a glare at him. "He's not a moron."

"He still let himself be beaten." The boss whirled away from the sight of their pursuer towards Sam. "Set him down and give him to me!" When Sam just gave him a confused look, he held out his hand in a gimme gesture with an accompanying growl that made his intentions fairly plain.

Sam quickly brought the hunter down from his shoulders, setting him on his feet. For a moment, Dean thought it would be the perfect time to get away as the giant released him. However, a vice-like grip clamped down on his arm. Surprised, Dean looked down and tried to tug himself away from the short man. He couldn't even budge him though.

Crowley was a lot stronger than he looked.

"Catch up with us quickly." The Brit ordered before he began to leave, tugging Dean behind him.

"Why? What do you want me to do?" Sam's face again scrunched with confusion.

Crowley looked back at him "Finish him! Your way!"

"Right." Sam turned in the direction they had come from. "What exactly is my way?" He muttered, not expecting his boss to hear him.

"Oh for Christ's sake!" Crowley immediately halted and turned towards the giant, bringing Dean to an abrupt stop. "You've got a gun!" He pointed it out. "When the man in the trench coat comes around the bend, shoot him in the bloody head!" He was yelling now. "Or if you want it to be a bit messier, hit him with a rock! I don't care, just get rid of him." Muttering curses, the man finally left with their prize.

Sam frowned at his retreating back. "My way's not very fair." He said to himself as he drew his gun and hid behind one of the convenient boulders.

All too soon, the mysterious man was making his way through the small field of boulders. He slowed down from his run as he carefully studied the ground. He frowned at whatever he saw, when suddenly a gunshot went off.

The man in the mask jerked back as rocks sprayed from where the bullet had embedded itself in the boulder mere inches from his head. He quickly turned to face where the shot had come from, instinctively drawing his blade.

Sam walked around from behind the boulder, still holding the smoking pistol. "I did that on purpose. I didn't have to miss."

Where the giant might have thought that the man would actually look at where his brains were nearly blown from his head, to his surprise, the man's eyes never left him. "I can believe that." He replied. Neither of them moved for a moment. Just as an awkward silence was falling, the man spoke again. "Now what?"

"We face each other as God intended… sportsmanlike. No tricks, no weapons, skill against skill alone." Sam offered.

The man's head tilted a bit, as he looked a bit bewildered. "You mean, you'll put down your gun and knife while I'll put down my sword, and we'll try to kill each other like civilized people?"

Sam cocked his pistol and aimed it at the man. "I could just kill you now." He reasoned.

The man pondered it for a moment before sheathing his sword. "It seems you really leave me no choice." He began to remove his sword from his belt.

"I'm glad you see it my way." Sam chuckled, as he too removed his weapons.

"It does seem like the odds are in your favor in hand to hand combat." The man in the trench coat finished setting down his sword, and pulled out a knife from his boot as well.

Sam nodded at the show of sportsmanship. "It's not my fault that I'm bigger and stronger than everyone."

"Though fighting doesn't seem to be your cup of tea as it were." The man straightened and studied Sam. It made the giant feel slightly uncomfortable.

"Well, I actually want to be a lawyer, but school costs money." He shrugged. "Crowley pays well."

"So you intend to become a purveyor of the law, and yet you do criminal acts." The man settled into a fighting stance. "That does not seem to be a good start for building a reputation."

Sam gritted his teeth. "I could just pick my gun back up."

The man wasted no more time. He came at Sam a lot more quickly than he had anticipated. The giant swiftly dodged the punch aimed at his face. He was surprised as it was followed up with a punch in the stomach. It hurt a bit, but Sam made sure none of the pain showed on his face.

Sam jumped back, hoping to get out of range, but the man managed to get around him and brought his hands together to land a blow across his back. Sam grunted and stumbled a couple steps forward. He quickly brought his hand up to block another punch, and managed to throw the man back a bit.

"Aren't you going to attack?" The man asked, as he paused in his attack. His head was tilted once more.

Sam faked a smile. "Just thought I would give you a chance, so you'd feel better."

In reality, he was hiding his surprise. Sure, Dean had presented an interesting challenge as it had been years since puberty hit and people willingly tried to brawl with him. This man was even better than the hunter though. One would think that he'd been training in combat all of his life.

This could be harder than Sam originally thought it would be.

This time, the giant was the one who took the offensive, but the man easily dodged, managing to slip a punch to Sam's ribs as he did so. Sam swung his arm out, hoping to catch the man as he went around his back. Instead, the man caught it and kicked at the back of the giant's knee, temporarily making the leg collapse. Sam quickly recovered and tried to grab the man once more, but he easily slipped past his grasp.

"You're quick." Sam couldn't help but acknowledge.

"And a good thing, too." The man replied as he attacked once more, Sam barely keeping up with his punches before the man retreated once more.

"Why are you wearing a mask?" Sam asked, truly curious. He took several swipes at the man, but continued to miss. "Did you get burned by acid or something?" The man actually bent fully backwards at his latest lunge, and used his momentum to flip himself over, his foot catching Sam right in the jaw. He couldn't help but be glad that he hadn't bit off his tongue as he rubbed his sore jaw. He growled though and doubled his efforts.

"It's quite comfortable. I could see it catching on." The man seemed to be hiding a smile; whether due to the conversation or Sam's inability to catch him, the giant didn't know. The man slipped under his guard once more as he crouched near the ground to avoid the clutching grasp of his hands, and he swept Sam off his feet with a kick across the legs.

Sam hit the ground hard, but rolled in order to avoid the next kick aimed at his head. He regained his footing. "And the trench coat?" He aimed a punch at the man's face. He was getting pissed and he didn't care how obvious the move was.

"I like it." The man easily caught the punch and used it to swing around and jump onto Sam's back. He wrapped his arms around the giant's neck in a chokehold.

Sam grunted from the pressure, but he had enough wits to back up. A stray thought occurred to him just as he hit one of the boulders, the pursuer getting the brunt of the blow. "I just figured out why you're causing me so much trouble." It also explained his initial challenge with Dean as well.

The man grunted. "Care to enlighten me?" His hold on Sam only grew tighter. The giant walked forward a bit in order to try to smash the leech again.

"I don't fight most people one on one. I specialize in…" He groaned as he hit another rock with his back, but the man wasn't letting go. "Groups." Sam finally finished his sentence.

"What's the difference?" The man cried out as they hit another boulder.

Sam stumbled forward. "You use different moves when you're fighting half a dozen people…" Spots were appearing in Sam's vision and he felt a large sense of vertigo, "than when you have to be worried… about… one." With those final words, Sam's eyes finally rolled up into his head and he collapsed face first onto the ground.

The man quickly unleashed the giant and rolled him over. Pressing his ear to Sam's chest, he made sure that there was still a heartbeat. He lifted his head, satisfied that he had not killed him. "I apologize for the headache you will have when you awaken. Rest well for now though."

With that, the man quickly collected his sword and continued after Crowley.

Meanwhile, over at the ruins, a different man studied the ground where the fight had taken place. Prince Michael crouched down and looked over the scuff marks as Head Guard Raphael, Count Metatron, and his bodyguard Gadreel waited with the soldiers they had brought with them.

"There was… a mighty duel." Michael placed his own feet within the marks and mimicked some of the footwork that had been done.

"Who won? How did it end?" Metatron actually looked interested for the first time since they had dragged him from his work to accompany them. He always loved a good story.

Michael followed the trail until he got to where the entrance would have been. He stood slowly, his eyes tracing paths that no one else present could see. "The loser… ran off alone. And the winner…" He pointed off into the distance. "Followed those footsteps to Hell."

"Shall we track them both?" Raphael asked, ready to signal the men.

Michael waved his hand dismissively. "The loser is nothing; only the prince matters. Anna would kill us all should we lose him." He looked thoughtful for a moment. "Clearly this was planned by soldiers from Hell. We must be ready for whatever lies ahead."

"Could this be a trap?" Metatron asked almost nervously, his eyes darting from side to side. Gadreel rolled his eyes at his cowardice.

Michael quickly mounted his horse. He glanced at both his head guard and the count. "I always think everything could be a trap." With a flick of the wrist, the reins snapped and his horse quickly sprang into action. "It's why I'm still alive."

With those final words, the men made their way into Hell.

**Notes for the Chapter:**

> AN: As you might notice I changed a few things about this scene, because unlike Fezzik, I think Sam actually works out and I also tried to explain why he'd work for Crowley in the first place. And of course, Michael's making his move.


	7. Mind Games

As the man in the trench coat came into a more open area, he quickly stopped. He tilted his head at the sight before him, unsure of what to make of it.

A table had been set up with a cloth covering it. Sitting on the table was a bottle of wine, two goblets, and even a basket of bread. For a second, all the man could wonder was where all of this had come from, since Crowley had not been carrying any of this with him. That was not what drew most of his attention though.

Crowley was sitting on the side opposite to him with a smug look on his face. Beside him was Dean, though a blindfold now obscured his vision. The boss had drawn his dagger, and the hunter sat absolutely still as the blade rested on his neck.

The man in the mask approached the table with caution.

"So it is down to you, and it is down to me." Crowley stated in a somewhat dramatic fashion. "If you wish him dead, then, by all means, keep moving forward." He pressed the dagger a bit harder against Dean's neck and the hunter gave a small gasp as it nicked him.

The man immediately stopped. He slowly raised his hands in the universal sign of surrender. "Let me explain – "

"There's nothing to explain." Crowley snapped, cutting him off. He shot the man a disgruntled look. "You wish to kidnap what I have rightfully stolen." He gestured at Dean with his free hand.

The man's eyes narrowed at that. "Perhaps an arrangement could be reached?" He asked reasonably enough. He took another step forward.

"There will be no arrangement, and you're killing him." Crowley's blade once more barely nicked the hunter. Truthfully, neither of the cuts was deep enough to even bleed, but the effect made the man stop all the same.

Crowley and the mysterious man simply stared at each other. "Well, if there can be no arrangement, then we have reached an impasse." He finally said. Crowley was glad, as the silence had been getting uncomfortable.

"I'm afraid so." The boss sighed. "I can't compete with you physically, and you're no match for my brains."

"And yet you managed to drag someone in chains all the way here." The man pointed out. Before Crowley could protest, he moved on. "You're that smart?"

"Let me put it this way: ever heard of Plato, Aristotle, Socrates?"

"Yes." The man tilted his head, trying to see where he was going with this.

Crowley snorted. "Morons, the whole lot of them."

"Really." The man's tone could have been sarcastic, but it had a monotone quality to it that made it really hard to tell. He was studying the Brit again as if trying to pick his brain apart with his eyes. "In that case, I challenge you to a battle of wits."

"For the princess?" Crowley asked.

"Hey!" Dean protested. Unknown to him, the man just rolled his eyes at Crowley's attempt at humor and nodded.

"To the death?" The boss tried to clarify. The man once more nodded. "Then I accept." Crowley sheathed his dagger, and gestured for the man to sit across from him.

"Good." The man settled himself, and after glancing over the table again, he waved at the wine. "Pour the wine."

As Crowley did so, the man took out a small vial from the inner pocket of his trench coat. He easily uncorked it, and held it out to the boss.

"Smell, but don't touch." He ordered as the other took it.

Crowley held it up to his nose and took a large sniff. He then raised an eyebrow. "I smell nothing." He said as he returned the vial.

The man in the mask held up the vial. "What you do not smell is Rowena's Bane. It is odorless, tasteless, dissolves immediately in any liquid, and is among one of the deadliest poisons known to man."

Crowley's face showed nothing. "I see."

The man picked up both goblets of wine and turned away from his opponent, fully blocking his sight with his body. In less than a minute, he faced the table once more and set the goblets down. One was in front of Crowley, and the other rested in front of him. "All right." He gestured at the two goblets. "Where is the poison?" He folded his hands delicately in his lap. "The battle of wits has begun. It ends when you decide and we both drink. We'll find out who is right, and who is dead."

The man's faced showed no emotion at all as Crowley smirked up at him. "But it's so simple." As he continued to talk, he gestured at whatever he was talking about. "All I have to do is divine from what I know of you: are you the type of man who would put the poison into his own goblet or his enemy's? Now, a clever man would put the poison into his own goblet, because he would know that only a great fool would reach for what he is given. Clearly, I am not a fool so I can clearly not choose the wine in front of you. But you must have known that I am not a fool, in fact you would have counted on it, so clearly I cannot choose the wine in front of me."

The man frowned at him. "Have you come to a decision then?"

"Absolutely not." Crowley countered. "Because Rowena's Bane comes from Scotland, as everyone knows, and Scotland is filled with wild and suspicious people. Therefore they are used to not trusting others, as I do not trust you, so I can clearly not choose the wine in front of you."

"Fascinating." The man said, his face still showing absolutely nothing though his eyes held a curious light to them. "It is interesting to see your thought process."

"Just wait 'til I get going." Crowley grinned at him, though it faltered a second later. He frowned. "Where was I?"

"Scotland."

"Yes, Scotland." The Brit recovered. "And you must have suspected that I knew the origin of the poison, so I can clearly not choose the wine in front of me."

"I believe you're stalling." The man deadpanned.

"You'd like to think that, wouldn't you?" Crowley pointed an accusing finger at the man. "You've beaten my giant, which means you're exceptionally strong. You could've put the poison in your own goblet, trusting in your strength to save you, so I clearly cannot choose the wine in front of you. However, you've also bested my swordsman, which means that you've studied. In studying, you must have learned that man is mortal, and so you would have put the poison as far away from you as possible, so I clearly cannot choose the wine in front of me."

The man tilted his head once more. "You're trying to trick me into giving something away." His head righted itself. "It won't work."

Crowley laughed. "But that's the point! It has worked! You've given everything away! I know where the poison is!"

"Then make your choice." The man in the trench coat simply said.

Crowley rubbed his hands together. "I will, and I choose – " Something caught his eye and he squinted at it. "What the bloody hell is that?" He pointed in the direction of his gaze.

"What? Where?" The man turned around, away from the table, in order to look at what Crowley had been pointing at. As soon as his back was turned, Crowley gleefully switched the goblets around. He chuckled to himself as the man turned back around. "I don't see anything." The man sounded a bit disgruntled.

The Brit shrugged. "My mistake. I could have sworn that something was there. No matter." He smirked at the man.

"So have you made your decision?" The man asked once more.

"Yes." Crowley confirmed. "Me from my glass," he picked up his goblet, "and you from yours."

The man nodded his assent and grasped his own goblet. Together, they drank the contents of their respected goblets.

As they set them down once more on the table, the man smirked. Pointing at Crowley, he said, "You guessed wrong."

Crowley couldn't hold it in any longer. He roared with laughter. "You only think I chose wrong! I switched glasses while your back was turned! You fell for one of the oldest tricks in the books!" He continued to laugh until it suddenly cut off abruptly. His body fell forward onto the table.

The moment his body hit the table, the man was up and at Dean's side. He quickly removed the blindfold. The hunter finally got a good look at the man who had been pursuing him relentlessly.

"Who are you?" He demanded, as the man pulled a set of lock picks from his pocket and got to work on the handcuffs.

"Someone not to be trifled with." The man replied as he freed Dean. He looked up into his eyes, blue meeting green. "And that is all you ever need to know."

The hunter averted his gaze by looking over at the table and Crowley's body. He pursed his lips. "And to think that your cup had been the poisoned one the whole time."

"They were both poisoned." The man said matter-of-factly. He pulled Dean to his feet as he returned the picks to his pocket. "I've spent the last few years building up an immunity to Rowena's Bane." With those final words, he grabbed Dean's arm and pulled him away.

As soon as they were gone, no one was there to see the body twitch and then sit up.

Crowley chuckled. "Put it in both glasses. How smart." He smirked as he held up his goblet before putting it down once more. "Rowena's Bane. If it were anyone other than me, it would have worked. After all," a bit of a Scottish accent slipped into his voice for a moment, "that witch practically raised me on the stuff."

He stood and looked off where the two had gone. "I'll give you this round, kid. The game was quite a lot of fun." He dusted off his clothes and withdrew a sack of money from his pocket. "I already got paid, so no worries." He pulled out a coin and flipped it. His eyes stayed on it as it twirled in the air. "These boys and their petty fights. Why on Earth would someone wish to have a kingdom…"

"Master Crowley?" Several men popped up with horses and supplies. They stood ready and waiting for their boss's command. The boss snatched the coin and pocketed the money, before moving over to his men.

Crowley smirked once more as he mounted his horse. "When you can rule the entire underground world?" He finished his earlier thought.

With that, he rode off, cackling evilly.

**Notes for the Chapter:**

> AN: Despite putting him in Vizzini's role, I couldn't kill off Crowley. He's just too smart for that. Actually, as he has survived to Season 11 on Supernatural without actually dying once (though he did fake his death like in here), I'm pretty sure one of the rules is that Crowley can't be killed off. I like this scene, and putting Crowley in it only made it better in my opinion. Next time, we'll get to find out who the man in the mask is (though we all already know). See you!


	8. Revelations

Michael didn't bother getting off his horse as he looked down at the dent that was left in the ground among the boulders.

"Someone has beaten a giant." He exchanged a look with Metatron. "There will be great suffering in Hell if he dies." With a flick of the wrist, they were off once more.

At the same time, the man in the trench coat and Dean were slowing down from their run. Up ahead there were some rocks, so the man nudged the hunter towards them. "Catch your breath." It wasn't clear whether it was an order or a suggestion.

Either way, Dean gratefully sunk down onto the nearest rock. He wasn't grateful for his so-called rescuer, but it had been a crappy day and he felt that he deserved to rest for a bit. He studied his latest kidnapper. There was something slightly familiar about him, but he pushed that aside to fuel his current annoyance.

Dean hated that he just kept being pushed around like some sort of helpless damsel in distress. He totally could have gotten away from those three.

Eventually.

Which brought him back to here. "If you release me, whatever you ask for ransom, you'll get it. I promise you."

The man had been watching behind them, hardly seeming to be even breathing hard despite his efforts to catch Dean and get away, but at the hunter's words, he turned to him. He frowned at him. "And what is that worth, a promise from one such as you?" He gave a huff of air that the hunter thought could be a laugh. "You're jokes aren't very funny, your Highness."

Dean's face scrunched up in confusion for a moment, because the guy was almost acting like some sort of jilted lover. He couldn't remember meeting him before though. He moved on. "I was giving you a chance." The hunter leaned back a bit and crossed his arms. "It doesn't matter where you take me. Michael may not be me, but he's still a decent hunter. He will find you."

The man tilted his head at him a bit. Again, it felt familiar. "Are you that anxious to return to the arms of your dearest love?" He asked somewhat bitterly.

"Anna's not my dearest love." Dean rolled his eyes. "But I know that Michael will find me."

A quick flash of confusion passed over the man's face; before the hunter could analyze it, he was talking again. "You freely admit that you do not love your fiancé."

"She knows I do not love her." Dean felt defensive for some reason.

"Perhaps you aren't capable of it." The man muttered, looking away. The hunter almost didn't hear it.

He bristled and stood. Dean walked over to the man, and was pleased to find that he was taller than him. "I have loved more deeply than a killer like you could ever imagine." He growled.

The man in the mask stared at him a moment, and then he stepped right into Dean's personal space, his eyes never leaving Dean's. Something in the hunter flinched, and even though he was taller than the man, it felt like the stranger was looming over him.

It was quite intimidating.

"You should show me some respect." The man's voice was dangerous and low. "I just pulled you out of a bad situation, but I could just as easily throw you into a worse one." He stepped back, and Dean felt like he could suddenly breathe again.

The man grabbed his arm. "Come."

They continued on their way.

Michael wasn't far behind as he picked up the vial still sitting at the table and gave it a sniff. "Rowena's Bane." He determined. "I'd bet my life on it."

The prince stood and examined the ground around it. "And these are the prince's footprints. He's alive, or at least he was an hour ago." He quickly mounted his horse, and looked over at Metatron. "If he is otherwise when we find him, I'm not the one who will be telling Anna."

The men quickly did noses and Metatron cursed, as he was the last one. Raphael and Gadreel gave him sympathetic looks, as they wouldn't want to be on the receiving end of the princess's wrath, but they didn't say anything.

They were close to their prize.

The duo stopped once more as they reached some rocks alongside a gully. "Rest, your Highness." The man in the trench coat again ordered.

Dean had been thinking about it since the guy had snatched him from Crowley's grasp, but finally, as he sat once more, the puzzle pieces fell into place. "I know who you are." He growled, anger bubbling under the surface. "You're mannerisms show everything. You're the Avenging Angel, admit it!"

The Angel smirked a bit and gave a bow. "With pride." As he straightened, he looked once more into Dean's eyes. "How might I be of service?"

"You can die slowly, cut into a thousand pieces!" Dean shouted, unable to sit any longer. He jumped up and paced back and forth. He was trying to get rid of his irritation, but this was the Angel. He could never forgive him.

The pirate pursed his lips, looking displeased. "That's not very nice." He replied. "What have I done to deserve your ire?"

The hunter stopped and turned to him. How could he not know? "You killed my love."

The Angel looked thoughtful. "It's possible." He admitted. "I've killed many men during my time. Who was this love of yours?" He walked over to one of the larger rocks and leaned against it. "Another princess like this one, rich and a nice figure?"

"No." Dean said softly, wistfully. His eyes gazed off into the distance. "A stable boy. Poor, with eyes like the sky on a sunny day." He paused, returning to the present, and turned to send an accusing look at the pirate. "Your ship attacked him as he was returning home. And the Avenging Angel never takes prisoners."

"I can't afford to make exceptions." The Angel replied. "If people heard word that a pirate went soft like that, they would disobey. Then it would simply be too much work." His face showed how that thought didn't agree with him.

Dean growled. How dare he! "Screw you." His voice was low as he said it. "You can't make fun of my pain!"

The Angel gave Dean a serious look, no mischief in his eyes. "Life is pain, your Highness." His tone brooked no argument. "Anyone who tells you otherwise is selling something." He stood up straight and appeared thoughtful again. "I think I remember this stable boy of yours. It would have been about 5 years ago now?" He seemed to be searching for something as he looked up into Dean's face. "Does it bother you to hear?"

The hunter turned away petulantly. "Nothing you say can upset me."

"He died well. That should please you." The Angel said, nonchalantly. He continued as if he was simply talking about the weather and his natural monotone wasn't helping. "No bribe attempts or blubbering. He simply said, 'Please, I need to live.'" Dean watched from the corner of his eye as the pirate turned towards him. "It was the please that caught my memory. Most aren't polite to pirates as you can guess. I asked him what was so important. 'True love,' he replied and he even smiled a bit."

The hunter's breath caught, as he knew exactly what he was talking about.

"He went on to talk about a boy that was amazing and beautiful and faithful. I assume he meant you." The Angel huffed out a laugh again. "I guess you can thank me for killing him before he found out what you really are."

That jolted Dean from the stupor he had fallen in. He turned back to the pirate. "And what am I?"

The Angel's eyes didn't leave him. "He spoke of faithfulness." He stepped closer, in Dean's space once more. "Tell me, when you found out he was dead, did you get engaged to your princess the very next day, or did you wait a week out of respect for the dead?"

"How dare you!" Dean growled. "You don't know anything! I died that day!" He paused for a bit as he took in the gully right behind the pirate. "And you can die, too, for all I care!" With those words, he pushed the Angel down the hill.

Dean was about to leave when that gravelly voice floated up to him from where the pirate was rolling down the hill. "As… you… wish!"

His stomach dropped and Dean whirled around. His eyes widened in realization. "Oh, my God! Castiel!" Without any more hesitation, he threw himself over and they rolled down into the gully.

Moments later, Michael and his entourage arrived at the top of the hill. The prince looked around, disgruntled. "They disappeared." He surmised. "Though unless I am wrong, and I never am wrong," a look at his cohorts prompted quick nods of agreement, "they are headed straight into Purgatory." He ignored their panicked looks as they rode off once more.

**Notes for the Chapter:**

> AN: Ta-da! Now I can stop writing "the man" or "the stranger" every other sentence. I know I cut out a lot of parallels to Buttercup's flowery language describing Wesley, but this is Dean Winchester so even that thing about Cas's eyes (which is true) is a bit much for him normally. I'm really trying hard not to make the characters too OOC while keeping in the spirit of the original material, The Princess Bride and Supernatural.


	9. Journey to the Center of Purgatory

The couple came to a stop at the bottom of the hill. Dean landed on top of Cas and looked down to see his long-lost love. The mask had fallen off while rolling down, so the hunter could clearly see those azure eyes he had longed for. He brought his hands up and cupped Castiel's cheeks, enjoying the feel of the stubble under his fingers.

Castiel was here, and he was alive.

"Are you injured?" Cas asked, a smile tugging at his lips. He looked up at Dean with all of the love and devotion that Dean had never felt he had deserved.

The hunter laughed. "Who cares? Jesus, Cas, you're alive!" He hugged Cas tight.

"I told you that I would return for you." Castiel returned the embrace.

Dean finally released him, and he just sat back and looked at him. A thought suddenly occurred to him. He punched Cas lightly on the shoulder as he also sat up. "What the hell was that up there? Were you trying to piss me off?"

Cas frowned at him. "I finally managed to return and I heard you were engaged to a beautiful princess." He looked away. "I wasn't happy, Dean."

"Well, I can guess that but still…" Dean failed for words as he could sense Cas's underlying anger and hurt. No one did passive aggressive like Cas could.

"Plus, it was Anna, a member of our royal family, of all people." Cas looked really disappointed.

"So she's the princess of our country. What's wrong with that?" He shrugged, but Cas gave him a deadpan look.

"Do you remember that war that started all of this?" Dean cringed at the thought. "It didn't start because Hell attacked us or anything like they said." Cas's face twisted slightly in disgust. "It started over a petty argument between Prince Michael and Hell's prince, Lucifer."

Dean found his mind was blank. He hadn't known that.

"How many people died due to their vanity?" Cas asked softly, looking off into the distance.

Dean's hands shook a little as he took Castiel's hands in his own. "I thought you were dead."

Castiel turned to him with a sad smile. "We share a profound bond, Dean. This is true love, and nothing can stop it. Even Death can only delay it."

Dean dropped his head into the crook of his love's neck, inhaling that scent that was almost forgotten. "I won't forget that again."

"You won't need to." With two fingers, Castiel tilted his head up and brought his lips forward for a passionate kiss.

* * *

Jimmy stopped reading for a moment and took a deep breath. "Claire, stop laughing." He said seriously.

Still, she couldn't help it. Claire lay on her bed, clutching her sides as giggles and chortles spilled from her lips. She rolled onto her side in an attempt to stop laughing.

Jimmy finally looked up and shot her an annoyed look. "This isn't even one of the funny bits. It's romantic."

"That's why – " Claire gasped for breath as her laughs finally subsided. "That's why it's so funny. This is such a chick flick moment." Another giggle slipped through. "Oh, my God. If he knew about this, he would die." She sat up as a thought occurred to her, all laughter abruptly stopping. "Does he know about this?"

Jimmy sighed. "I don't know." He gave her another look. "Is this going to be your reaction to every romantic scene?"

She shrugged. For her, it was more the image of this taking place that was funny than the actual scene.

He sighed again and flipped a few pages. "Let's just go straight to the next action bit since your generation clearly has no idea what good romance is."

"Hey!" Claire responded, mildly offended.

* * *

Dean and Cas raced through the ravine towards the forest of ancient trees. They clutched each other's hand even as the pounding of horse hooves sounded behind them.

"The prince is too late." Cas stated, as they closed in on the forest that most would not dare to approach. "A few more steps and we'll be safe in Purgatory."

"Yeah, safe is not the word that comes to mind when you say, 'Purgatory.'" Dean replied, feeling chills go up his spine just looking at the place. "I'm pretty sure this isn't something we can survive."

"You're only saying that because no ever has." Cas reasoned. "You were the one who was always telling me to think more positively."

"Being totally insane is not thinking positively."

"We're together though." Castiel looked back and gave Dean a small smile. "We can do anything." He gave his hand an extra squeeze.

The hunter blinked at him in surprise. Then, he sighed. "By God, you're turning me into a sap." Thus, the two of them entered Purgatory side-by-side.

They could tell the difference right away. Despite the fact that there was plenty of daylight left, the moment they stepped foot in the forest, the light hushed into an odd twilight. Everything seemed to have a gray cast to it, with occasional flashes of dull green. Strange sounds and growls came from all around them, but they forged onward, ignoring the twinges of unease in their souls.

As they traveled further in, Dean looked around thoughtfully. "Hey, this isn't too bad." Cas threw him a confused look and his usual head tilt. "What? I'm not saying that we should build a summer home or anything, but the trees are nice enough."

Cas raised his eyebrows a bit and shrugged and they continued forward. As they pushed forward, the couple heard a thumping noise approaching them. They looked around nervously, and suddenly a spurt of fire appeared right next to Dean.

He yelped and jumped back, but not before his outer shirt caught on fire. Cas quickly helped the hunter yank it off and then they stomped on it until the flames were out.

They stood there panting as the collected themselves. Finally, Cas gently took Dean's arms and studied them for burns. "Are you all right?"

Dean nodded. "And you?" The pirate nodded. "Well, that was fun." He said sarcastically.

"Indeed." Castiel replied as they moved onward. "Purgatory certainly keeps you on your toes."

Before long, they encountered a corridor of vines blocking in their way. Cas drew his sword and took the lead to hack through them. As he did so, he spoke to try to encourage Dean. "This will soon be something that we can look back on and laugh." He grunted as he had to saw through a particularly thick vine. "Because the Angel's ship, Singed Wings, is anchored at the far end. And I, as you know," he looked back at Dean, "am the Avenging Angel."

"Yeah, I don't get that." Dean said, tossing the cut vines to the ground. "How is that possible when the Avenging Angel's been at large for twenty years, and you only disappeared five years ago?"

"Life takes humorous turns at times." Cas put down his sword for a moment as the familiar thumping sound came near and he drew Dean away from the flame spurt. He picked it up as they went forward. "You see, the story about saying 'please' was true." More vines blocked their path, but the pirate easily cut them down. "It intrigued the Angel, as did my devotion to you. Finally, he said, 'All right, Castiel. I've never had a valet, so we'll try it for tonight. I'll most likely kill you in the morning.'

"This continued for three years. 'Good night, Cassie; nice work. Sleep well for I'll most likely kill you in the morning.' It actually worked out quite well for me." Castiel paused so that way they could make their way over a log, ignoring Dean's raised eyebrow at the nickname. He continued once they were back on the ground. "I was learning even more about fighting than I did in the army and much more, anything anyone could teach me. The Angel and I actually became friends during that time. Then it happened."

Castiel paused as he squinted at a suspect part of the path in front of them, and carefully stepped around it. Dean followed his lead, but when he didn't start back up, the hunter felt the need to prompt him. "What happened?"

Cas blinked. "Oh. Well, the Angel had grown so rich he wanted to retire. So he took me to his cabin and revealed his secret. 'I am not the Avenging Angel,' he said." The pirate paused at Dean's look of surprise before continuing. "'My name is Balthazar. I inherited the ship from the previous Avenging Angel, just as you will inherit it from me. That man also was not the real Avenging Angel either, but a man named Hannah. The real Avenging Angel was named Joshua and he had been retired for fifteen years and living like a king in Turkey.'"

The next set of vines was easily moved out of the way like a curtain, so Cas sheathed his sword. "Then he explained that the name was important to inspire the necessary fear. No one would surrender to the Avenging Castiel. So we sailed ashore, got a new crew, and he stayed on for a while as first mate and established my identity as the Avenging Angel.

"Once the crew believed, he left and I've been the Angel ever since." Castiel stopped what he was doing and faced Dean, taking both of his hands. "Except now that we're together, I shall retire and hand the name over to someone else. Capisce?" His blue eyes stared into Dean's, showing his complete sincerity.

Dean smiled. "I capisce." He decided that he would take the lead now, as they were through the vines. However, the moment he put his foot down, he felt nothing to take his weight and promptly was sucked into the sandpit.

Castiel sprang into action. He cut one of the vines and grasped it in one hand as he dived after Dean. For a long moment, all was still. It was almost as if the entire world was holding its breath. In the distance, a howl echoed through the forest, but there were no other sounds.

Then a hand burst from the depths, climbing up the vine, and the sand fell back to reveal Cas clutching onto Dean with one hand while following the line of the vine with the other. He pulled them out and away from the lightning sand, and for a moment, they just lay there, wrapped up in each other, panting.

Dean groaned. "I am so sick of being the stupid damsel in distress." He grumbled.

"You're beautiful enough to be one." Cas pointed out helpfully. He frowned as he heard a growl, and he rose up a bit off the ground. In the corner of his eye, he caught sight of something large and black. He warily glanced around.

"That surprisingly doesn't make me feel better, Cas." Dean said as he rolled over to push himself up. "I'm getting the feeling that we're going to die here."

"Don't talk like that. We've survived a lot already." Castiel pulled himself to his feet and dusted himself off. He gave Dean a hand up, while still keeping a close watch. As the hunter brushed himself off, he drew his sword just in case. They carefully made their way forward. "After all, what are the three terrors of Purgatory? One, the flame spurt, which we can avoid since there's a popping noise before each one. Two, the lightning sand, but thanks to you, we know what that looks like and can avoid that too now."

"Uh, Cas." Dean stopped the pirate by placing his hand on the other's arm. "What about the Double H?"

"The Hell Hounds?" Cas asked to clarify. At Dean's nod, he said seriously, "I don't think those exist."

At that moment, with a howl and a growl, a Hell Hound burst out in front of them. It looked like a large, black dog, but its eyes were red and blood seemed to be caked into its matted fur.

The Hell Hound lunged at Cas, knocking him over. It aimed to bite his neck, but the pirate quickly blocked with his forearm. He grunted as its teeth ripped into him. The injury caused him to drop his sword, making it useless.

Meanwhile, Dean immediately acted. As the Hell Hound was biting Cas, he picked up a branch and gave the thing a good whack. It let go of the pirate, and instead turned its attention towards the hunter. He fended it off with the branch, but one hit broke it in two.

After being let go, Cas scrambled to his feet. When Dean began cursing over his broken weapon, he drew back the attention of the beast with a swift kick to its rear. The beast pounced on him once more, its claws raking across his shoulder. He ignored the pain though as Dean tried to find the sword so they could kill the Hell Hound. Still, as he struggled with it, he heard a familiar popping noise. Blocking out the hunter's cry of surprise, he rolled with the beast and landed just so the Hell Hound got caught in the flame spurt.

The Hell Hound cried in anguish. Castiel used the distraction to get away from it and as he did so, his hand fell upon his sword. Scooping it up, he stood and stabbed the beast three times until it fell over dead.

Both of them stood there panting for a moment. They exchanged a look that told each other that they never wanted to do that again. They straightened and went on their way, prepared for anything.

When they finally exited Purgatory, they were holding hands. Dean took a deep breath as even the air seemed sweeter outside of that forest.

"We did it." Castiel had a small, satisfied smirk on his face. His whole aura just exuded the sentiment that he had been right all along.

Dean chuckled. "Yeah, I guess that wasn't too terrible."

The two of them leant in to kiss, but just then, several men on horseback rode up towards them. Cas raised his sword and pulled Dean behind him as they quickly formed a half circle in front of them.

"Okay. Maybe I spoke too soon." Dean admitted.

**Notes for the Chapter:**

> AN: Wow. I didn't realize how long this one. I think it almost beats the Gabriel vs. Cas chapter. Still, I hope their reunion lives up to expectations. Still, I think it is kind of funny, because this entire movie really is one giant chick flick moment, so Dean would be appalled to be part of that. I'm glad you like it and I'll see you next time.


	10. Separation

Michael was smug as he rode up with Metatron, Raphael, and Gadreel in tow. He looked down on the couple as his horse halted. "Surrender!" He ordered.

Castiel lifted a domineering eyebrow. "You wish to surrender to me?" He nodded. "Well then, I accept."

Gadreel snorted at his reply, but quieted when Michael leveled a glare at him. The prince turned back to his prey. "I'll give you marks for bravery." He admitted. "But don't be a fool."

"How are you proposing to capture us?" Cas pointed out, beginning to back up ever so slightly. "We know the ways of Purgatory. We can live there quite happily for some time, and if you feel like dying, you could always visit us."

Movement caught Dean's attention from the edges of his peripheral vision. Turning towards it, he saw soldiers aiming at Cas with crossbows. He was about to warn his love when he saw that they were also on their other side. Dread washed over him.

"I tell you again to surrender!" Michael continued to talk, not seeing that Dean had begun to notice his trap.

"I refuse." Castiel held his ground.

"For the last time, surrender!" Michael shouted.

"I'd rather die first!" Cas tightened his grip on Dean's hand.

"Will you promise not to hurt him?" Dean asked as he drew his gaze away from those crossbows to face Michael.

The two men snapped out of their staring contest. "What was that?" Michael asked.

"What was that?" Cas echoed him, turning towards Dean.

Dean straightened and tried to look a lot tougher than he felt at the moment. He released Cas's hand and pulled away. It was really hard to ignore the heartbroken puppy dog eyes that were suddenly directed at him. "If we surrender, will you promise not to hurt this man?"

Michael studied him for a moment before raising his right hand. "May I live a thousand years and never hunt again."

"He's a sailor on the pirate ship Singed Wings. Promise to return him to his ship." Dean demanded.

"I swear it will be done." Michael vowed. As Dean turned to say his goodbyes, the prince leant towards Count Metatron. "Once we're out of sight, take him back to Heaven and throw him in the Pit of Despair." He ordered.

Metatron smirked. "I swear it will be done, sire."

Gadreel sighed, knowing who would actually be doing the work.

Dean grabbed Cas's hand once more, and looked down into those blue eyes that showed pain at what was unfolding. "I thought you were dead and it almost destroyed me." He lifted one hand and caressed his cheek. Castiel closed his eyes and leaned into his touch. "I couldn't live with myself if you died when I could have saved you."

"Dean…" The hunter didn't know what else would have come after that, for the prince hauled him onto his horse and swiftly left the scene. Most of the guards went with them.

Very few remained when Metatron turned to Gadreel. "Gadreel, if you will." That gleeful smirk remained on the count's face as he gestured at the pirate.

Gadreel sighed and moved his horse forward. He looked at Cas with pity in his eyes. "Come, sir, we must return you to your ship."

Cas gave him a once over and then responded with a small, sad smile. "We are men of action." He replied. "Lies do not become us."

Gadreel sighed once more. "Well spoken, sir." The knight shifted uncomfortably as Castiel's gaze fell on his right hand and never left. "What is it?"

"You have six fingers on your right hand." Castiel observed. His eyes shifted to meet Gadreel's. "I know someone who is looking for you." He glanced at the count. "Or more accurately, for your boss."

Gadreel didn't know what to make of that, so he did as Metatron had ordered and knocked Cas out with the hilt of his sword.

Darkness fell over the pirate.

When Castiel awoke, even before he opened his eyes, he realized that he was strapped down to a hard surface. He tested the bonds a bit, to see how strong they were, but found that they were too thick for him to so easily break. Therefore, he opened his eyes to gain more information.

He soon saw that he was in some kind of dungeon. He was strapped to a table, tied up with chains. There were various instruments of torture strewn around the place, but the one that he was unfamiliar with, and that was by far the strangest, was one that appeared to be some sort of machine. It had numbers along a lever, a waterwheel, and various things dangling from it. He had no clue what it was for. The sight of it made him uneasy though.

However, he took comfort in the fact that he still had his trench coat even if it was torn in places. He hadn't been lying when he said that he liked it.

The sound of a door opening and shutting drew his attention to the stairs that lead upward. A woman with red hair that was tied up in a bun was making her way down, and she was dressed as a nun, though she was missing her habit. She held a bowl of what smelled like medicine. When she saw Castiel was awake, she gave a large smile that was probably supposed to be reassuring. It only unnerved him further as it was empty and held no hint of sincerity.

"Hello." She greeted him as she came to stop beside him. "It's nice to see you awake." Without further ado, she began to treat his wounds.

Cas didn't even let a twitch escape as his injuries stung. With his face emotionless, he asked, "Where am I?"

"The Pit of Despair. I'm your nurse, Naomi." She said it so nonchalantly, as if it was no big deal. However, the name of the locale was quite alarming, though Castiel didn't give anything away. "Don't even think about trying to escape. The chains are too thick. And don't think about being rescued as only the prince, the count, his guard, and I know where this is." She continued to merrily fix his wounds.

"So I'm here until I die." Cas surmised.

"Until they kill you, yes." Naomi replied. "Though don't worry, I'll continue fixing you so that probably won't be for a while."

Cas couldn't help but stare at this woman. "You're healing me just so they can torture me longer?" Surely she had to be insane.

Naomi thought about it a moment. "Yes."

"I can endure torture." Castiel couldn't help but point out. She looked surprised but shook her head in disbelief. "You don't believe me?"

"Oh, you poor child." Naomi sighed. She gently caressed his cheek, which made Cas feel very uncomfortable and caused goose bumps to break out over his skin. "You must be very tough and brave to survive Purgatory. However, no one can withstand," her eyes raised to the mysterious, unidentifiable torture instrument, "the Machine."

Castiel really didn't like the sound of that.

Meanwhile, Dean was sulking in the castle. Due to the incident, he had been banned from riding Impala, and he was going stir crazy from having nothing to do. He stomped through the halls and pouted in corners, all while saying he was doing nothing of the sort. Anna's continued attempts at flirting were not helping his mood. There was only one person he wanted.

Michael and Metatron observed one of these incidences as Anna yelled at Dean once more for his lack of interest and the hunter stomped off in the opposite direction. The count sent the prince a questioning look.

Michael rolled his eyes. "He's been like this ever since Purgatory. It must be from the trauma."

"Of course." Metatron replied. And the two went on their way.

Anna's impatience had grown though, and due to her persistence, before the next day dawned, Anna and Dean were married. The next day at noon, he was presented once more to the people, only this time as a legitimate prince.

* * *

"Wait a minute, what the hell?" Claire burst out. She nearly let some of the chicken noodle soup she was eating spill out of her bowl.

"Hmm?" Jimmy tried to quickly chew the rest of the bite of his sandwich as he looked up at his daughter. "Problem?" He asked as he swallowed.

"You had to read that wrong!" Claire protested. "There is no way in hell that Dean would marry Anna! They have absolutely no chemistry! This is a freaking romance, so it should be Cas! Otherwise, with all the crap that guy has gone through for him, it wouldn't be fair."

"Life isn't fair." Jimmy pointed out. "I often have to point that out for you."

"Yeah, well, this is complete crap!"

"Do you want me to go on with this?" Jimmy raised an eyebrow at his daughter's antics.

Claire slumped down a bit and sipped more of her soup. "Fine. Go on."

"Good. Now no more interruptions." Jimmy raised the book once more.

* * *

"Citizens of the Kingdom of Heaven." Michael announced from the balcony overlooking the courtyard. "Very soon, I shall be crowned as king due to this auspicious event. For now though, let us congratulate the happy couple: Princess Anna and Prince Dean." With a wave of his hand, the guards opened the door and the newly weds walked out on the red carpet to be among the people.

The people clapped and cheered at them as Dean frowned. After all, this didn't feel right. However, as the cheers died down, people stared in shock as a new sound could be heard.

Someone was booing.

Everyone turned toward it, Dean included, and he felt a jolt as he recognized the woman booing.

It was Meg, the butcher's daughter from their village who had a tendency to be cruel but had always had a soft spot for Castiel.

"Boo! Boo! Boo!" She called out, a look of disgust on her face like someone had tried to sell her a piece of rotten meat.

"Meg?" Dean asked. "Why are you doing this?" The two of them hadn't always got along, but they had tolerated each other for Cas's sake.

Meg pointed an accusing finger at him. "Because you had love in your hands, and you threw it away! You broke my unicorn's heart after everything he did for you!"

Ice chilled through his veins. "They would have killed Cas if I hadn't done it." The hunter tried to justify his actions.

"Excuse me?" Meg crossed her arms. "Your true love lives! And yet you marry another." She waved a hand at Anna. She turned and appealed to the crowd. "True Love saved him in Hell and Purgatory, and he treated it like garbage."

The crowd was looking at him in disbelief. Disgust began to fill their eyes.

Meg turned back to him, and threw her dark hair over her shoulder. Her eyes met his and she gave the clincher. "I really should have taken Castiel for myself."

Dean gasped as he startled awake. He sat up in bed as he realized what he had to do. He quickly threw on his robe and headed towards the prince's office.

The wedding was ten days away, but he couldn't let this go any further.

* * *

"I told you so."

"No one likes a smart aleck, Claire."

**Notes for the Chapter:**

> AN: I feel like Meg legitimately had feelings for Castiel. I know Cas cared for her, but it wasn't really returned. Still, out of all the potential love interests people have brought up for Cas, I feel like Meg was the only one who could really compete with Dean.
> 
> We're half-way through!


	11. Plots and Torture

Anna was just going over some last-minute decorations needed for the wedding with Michael and Metatron as Gadreel stood in the corner, when Dean burst into the room. The three at the desk looked up at him.

"Dean!" Anna smiled and ran up to him holding the designs. "We were just – "

"I'm sorry." He told her. "But I can't do this."

She froze in shock. "What?" The question fell from her lips.

Dean looked past her and over at Michael and Metatron. "Look, it comes down to this. I love Castiel." He stammered a bit at that. It was such a girly thing to say, so he didn't admit it often. Still, he continued strong. "I always have, and I know I always will." He turned more towards Anna. "Princess or not, if you tell me that I have to marry you in ten days, I can guarantee that I won't be here, one way or another."

Anna went to open her mouth to reply, looking indignant, but Michael cut her off, drawing Dean's attention. "We would never wish to cause you grief." He moved from behind his desk to approach the hunter and his sister. "Consider the wedding off for now." Anna looked like she was ready to stab someone, but the prince ignored her. He turned to the count. "You returned this Castiel to his ship, correct?"

"Of course," Metatron confirmed, smiling a sickly smile.

"Then we will just alert him." Michael said.

However, Anna could not be silent for any longer. "Are you sure he even still wants you?" She crossed her arms, looking furious. Either at Dean for trying to break the engagement or at Michael for making the decision without consulting her, it didn't matter. "You were the one who did the leaving in Purgatory. Besides, pirates aren't known to be men of their words."

"When Cas says something, he means it." Dean looked her right in the eye, so she could see the conviction in his eyes. "He will always come for me. It doesn't matter where I am, because he'll find me."

Anna looked as if she were ready to throw down right then and there. Michael interfered before anything could happen. "I suggest a deal." He stepped between them, facing Dean. "Write four copies of a letter. I will send my four fastest ships, one in each direction. The Avenging Angel is usually close to Heaven at this time of the year. We'll show the white flag and deliver your message." He clapped Dean on the shoulder. "If Castiel still wants you, then bless you both. If not, then" he leaned close to Dean, "please consider at least making my sister happy. Agreed?"

Dean gave him a side-eye, but nodded. With that done, he left to go about his day.

For a moment, none of them moved. Then, Anna whirled on her brother. "You're not going to send those letters."

Michael opened his mouth to protest, but she cut him off.

"It's not like you were going to anyway, but I'm telling you." The redhead got up in his face. "You are not going to send those letters." She stepped back and moved to the door. "The wedding will go on. Oh, and," Anna turned back to look at him, "I don't know what you're plotting, but it will wait until I have had him."

"Do you love him that much?" Michael asked, somewhat surprised. He had never seen his sister like this.

"Love?" She snorted. "Have you seen his face? And his body?" Anna gave a breathy sighed, and looked into the distance with a dreamy look on her face. "I want him in my bed." She finally said as she snapped out of it. "Despite his reputation, he refuses to lay with me; whether because of this nuisance or because I am a princess, I don't know." She left. "See you later, brother."

Metatron and Michael exchanged a look.

Minutes later, the two were walking around the edge of the forest that surrounded the castle. Gadreel had stayed behind to make sure that the hunter didn't try to make a break for it. They slowed as they entered a grove.

"Your sister is too scary." Metatron said with a shudder.

"I guess the saying is true about not messing with redheaded women." Michael mused. "Though I must admit that she does have excellent taste."

"Ah, yes." Metatron smirked. "The hunter."

"He is much beloved by the people." Michael stopped, and turned to Metatron. "You know, it's odd, but when I hired Crowley to kill him after their engagement, I thought I was being clever. But it's going to be so much better if I strangle him after their wedding night. I can avoid Anna's wrath, and once Hell is blamed, the nation will be truly outraged." The prince smirked. "They'll be begging to go to war."

Metatron returned the look as he walked over to a tree that was filled with knots. He started to prod them. "Where is that secret knot? I always forget… ah." He managed to press it, and a door opened in the tree to reveal a passageway going down. The count turned to Michael. "Will you be coming down to the Pit? Castiel's gotten his strength back, so I'm starting him on the Machine tonight."

Michael gave a disappointed sigh. "I love watching you work, Metatron. However, I've got a wedding to arrange, a brother-in-law to murder, and Hell to frame for it. I'm swamped!"

The count threw him an understanding nod. "I understand." He clapped the prince on the shoulder. "Get some rest. If you haven't got your health, you don't have anything."

The two parted ways. Michael headed back to the castle, and Metatron walked down the stairs into the Pit of Despair.

Naomi was already rolling Castiel on a cart in the direction of the Machine. She began to hook him up to it, with what he now saw were suction cups, as Metatron walked in. The count gazed up at the Machine.

"Isn't it beautiful?" He asked the pirate, pride and adoration in his eyes. "It took me half a lifetime to create it." Metatron stroked the machinery. "Ever since I was a boy listening to stories, I found the pain of the characters fascinating. I've built my whole life around my interest in pain, specifically other peoples'."

The manner in which the count spoke of his machine, as well as other peoples' pain, made a chill run up Castiel's spine. He did not have a good feeling about this.

"I'm even adding my own two cents by writing the definitive work on it." Metatron moved behind a desk, and put a pen to paper. "I want you to be totally honest with me about how the Machine makes you feel. This being your first time, I'll use the lowest setting."

With a nod from the count, Naomi moved the lever from zero to one. Water was directed in and the waterwheel began to turn. At first, Cas wondered what this was all about, but then it hit him.

"Ah." He gave out small choking noises. Agony flashed through him. He had never felt such pain before. It felt like something was being drawn out of him, and a smarting sensation filled his entire body. He writhed on the tabletop of the cart; however, there was no way to escape the pain.

As his spasms died down, the nun moved the lever back to zero. For a moment, Cas could only lay there breathing.

"As you know, the concept of the suction cup has existed for ages." Metatron excitedly explained. "The only difference here is that instead of sucking water, I'm sucking life." He leaned forward. "I just sucked one year of your life away. I might one day go as high as five, but even I don't know what that'd do." He giggled in glee at the thought.

"Now," the count grew serious, "what did this do to you?" He renewed the ink on his pen, before looking up at his victim. "Tell me. And remember, this is for posterity, so be completely honest. How do you feel?"

Castiel could only make himself breathe. He couldn't even begin to form words. He shut his eyes in order to try to ride out the aftermath of his torture.

"Interesting." Metatron said, and he began to scribble down notes.

Cas couldn't help but pray that this would end sooner rather than later.

**Notes for the Chapter:**

> AN: And now I'm realizing that I'm posting a chapter about Cas getting tortured, when he is being tortured on the show. Isn't it weird that when it happens on the show, we're all shouting, "No!" but then we still put him through the wringer in our fan fics. Interesting. Anyway, I know Anna's more of a b*tch in this than she was on the show, but she's one of the villains as I've split Humperdink's role between her and Michael. Heck, in the show, we barely know Michael's personality besides the fact that he always follows Daddy's rules, and he's kind of a dick. In any case, onward and upward!


	12. Together Again

"You called for me, sire?" Raphael asked as he entered the prince's office and made his way over to the desk.

"Ah, Raphael. Good." As the large man stood next to him, Michael gave a quick look around before leaning forward. "As the head guard of Heaven, I trust you with this secret." He whispered. "Killers from Hell have infiltrated the Thieves' Forest and plan to murder my future brother-in-law on his wedding night."

Raphael's brow furrowed at the words. "My spy network has heard no such news."

"Any news yet?" Dean said from the doorway.

The two jumped and quickly stood. Michael hoped that he had not been overheard. "It's too soon." He replied with a stiff smile.

The hunter narrowed his eyes in suspicion, but continued on his way.

The prince and guard returned to their seats, leaning into each other's space for the sake of secrecy.

"He can't be murdered. Anna would be devastated." Michael said with great urgency. "On the day of the wedding, I want the Thieves' Forest empty, and every inhabitant arrested."

"They won't like that." Raphael pointed out. "They'll resist and my regular force won't be enough."

"Then, hire a brute squad!" Michael ordered. "I want that forest empty!"

"It won't be easy." Raphael admitted.

"Try ruling the world sometime." Michael said, and though he wasn't sure, Raphael almost thought that he wasn't joking.

Back in his chamber, Dean paced around.

"Something wrong, Dean?" Charlie, the maid who had been assigned to him, asked as she finished making the bed.

"Yeah, something's rotten in the state of Heaven." He groused. Though it had been weird at first, the hunter had grown to like the quirky girl. She was like the sister he had never had. "But I've got no clue what it could be."

"Hmm." Charlie brushed a lock of red hair back into her cap. "Want me to poke around a bit? After all, if you do it, you could get kidnapped again." She teased.

"Could you please?" He asked.

She saluted. "Roger!"

And yet, despite her and Dean's efforts, which involved a lot of sneaking around and spying on Charlie's part and constant escape attempts on Dean's part, the wedding came all too soon.

The day of the wedding had arrived. The brute squad had its hands full carrying out Michael's orders as the residents of the Thieves' Forest fled and fought back. One fought even more than the others.

"Ha!" Gabriel spun around and took out another adversary. His sword glinted in the sunlight as it zinged back and forth, cutting his opponents. His eyes were alight with the shine that only comes from a sugar high.

"This guy is crazy!" One of them ran away without even trying to fight him.

"I'm waiting for you, Crowley!" Gabriel called out as he took out another guy. "You told us to go back to the beginning, so here I am!" He laughed as he sliced and diced. "Just try to move me!" He challenged them.

"Surrender!" One of the men trembled a bit as he gave the order. "The prince gave his orders."

Gabriel stopped for a moment. "I'm under orders, too." His voice wasn't jubilant any more. "When the job goes wrong, you go back to the beginning. This is where we got the job, making it the beginning. I'm staying here." He blinked a bit as he began to feel tired all of a sudden.

The only soldier that hadn't gotten away grit his teeth and looked around. He seemed to find what he was looking for as he called, "Hey, brute, come here!"

"I'm waiting for Crowley." He mumbled, his energy fading away.

The swordsman heard a familiar chuckle. "You just get in trouble wherever you go, don't you?" Strong arms wrapped around him, and Gabriel let himself lean against them. He brought up a hand to touch the chest that was holding him up. "Hey, what are you touching?" The voice was a mix of indignant and embarrassed.

Gabriel looked up and grinned as the pieces fully fell in place. "It's you."

"Yep!" Sam grinned back. Without looking up, he punched out the brute that tried to interrupt their reunion. "You don't look so good." He noted, taking in the swordsman's punch drunk features.

"Pfft!" Gabriel waved a lazy hand. "I feel fine."

"Uh-huh." Sam's tone conveyed his disbelief as surely as his bitch face did. He pulled his arms away and Gabriel took a few staggering steps and then collapsed face first. The giant sighed.

This hadn't been how he had imagined meeting Gabriel again.

Sam took care of Gabriel as he recovered from his crash after eating too much sugar. As he did, he told Gabriel of Crowley's disappearance, the discovery of the six-fingered man, Gadreel, and more importantly, his boss, Count Metatron. Considering Gabriel's lifelong search, Sam thought he handled the news surprisingly well.

Gabriel promptly fainted. Though that could have been more from the health food the giant was trying to shovel into his mouth. Just looking at it caused shudders of disgust in the swordsman's candy-coated soul.

Sam took great care in reviving Gabriel. And when he said great care, he meant he dunked Gabriel's head in a bucket of water. Several times.

"Okay, that's enough!" Gabriel spluttered. The giant released him and the swordsman walked a few steps away, slicking his hair back. "Okay, so where's Metadouche now, so I can kill him?" He asked.

"He's in the castle with the prince. But the castle gate is protected by thirty men." Sam pointed out since he could see the vengeful gleam in the other's eyes.

Gabriel kicked the tub that was in the corner of the cabin. He couldn't help but feel frustrated by this latest hurdle. He was closer than he ever had been before. He turned to Sam. "How many can you handle?"

The giant thought it over for a moment. "Probably not more than ten."

"That'd leave twenty for me. Even at my best, I can't take that many." Gabriel ran his fingers through his hair. "Ugh, we need Crowley. I'm not that great at strategy."

"You plan stuff all the time." Sam countered. He hated seeing his friend so down.

"Yeah, pranks and tricks. This is a whole different ball game." Gabriel sat down and rubbed his forehead. He just needed to think this through.

"Crowley's gone though. He probably retreated to one of his hidey holes to wait for this to blow over." Sam complained, a bit miffed at how their former boss had left them in the lurch.

However, a brand new idea was sparking in the swordsman's brain. "No, not Crowley." He said in realization. "I need the man in the trench coat."

Sam glanced over at him. "What?"

"Look," Gabriel leapt up in excitement. "He bested you in strength. He bested me in steel. And if Crowley's in hiding, it's because that man out-thought him." He grabbed Sam's arm and bounced a bit. "And a guy who can do that can plan my castle onslaught any day." He grabbed his sword. "Let's go!"

"Where?" The giant looked at his friend, confused.

"To find the man in the trench coat!"

"But we don't know where he is!" Sam pointed out.

"Who cares?" Gabriel hovered in the doorway. "At long last, my father's soul will rest easy. Let's go kill!" He bounded out the door.

Sam gave an exasperated sigh. "Why do I always end up following that idiot?" He asked himself, but he still followed him out.

Over at the castle, Raphael presented himself to the prince.

"The Thieves' Forest has been cleared, and thirty men guard the castle gates." The head guard reported.

Michael looked up from sharpening his dagger. "Double it." He ordered. "Or else you will be explaining to Anna how her husband died."

Raphael audibly gulped, but remained stoic. "The gate only has one key," he held up the key on a chain around his neck, "and I carry it."

Michael smirked.

Everything was going according to plan.

**Notes for the Chapter:**

> AN: So not much really going on in this chapter besides Gabriel and Sam's reunion. As you probably noticed, I also added Charlie in because 1. I love her character and 2. Dean deserves an ally in the castle. I didn't want him to wait around to hear for news because that's not really his personality. Dean's a doer and despite what's been going on, he is no damsel. He would be trying to figure something out though Michael would put a lot of guards on him to prevent his escape. He'd at least try though.


	13. The Pit of Despair

As Raphael left to double the guard, Anna bounced in. "Today's the day!" She smiled.

"It is indeed." Michael picked her up and spun her around, her excitement infectious.

"Glad to see someone's excited." Dean said, slightly sarcastic, as he leaned into the doorway. His expression was the opposite of theirs.

"My darling!" Anna ran towards him, but before she could hug him, the hunter stopped her with an outstretched hand. She backed off, pouting at being denied her prize.

"In any case," the smile returned to her face, "we're getting married tonight. Tomorrow, we will be escorted to the channel by all of the army's men. Then, Michael's arranged for the entire armada to accompany us on our honeymoon."

"Except the four fastest." Dean cut in. At Anna's confused expression, he clarified. "Every ship but the four he sent."

The siblings shared a panicked look. "Of course," Michael said, "Yes, of course. All but those four naturally."

Realization dawned on his face as he looked between the two. "You never sent the ships." He glared at Anna. "And you knew. Don't bother lying." He seethed for a moment, but then he calmed down.

Somehow, that was even scarier.

"It doesn't matter." Dean said. "Cas will come for me."

"He won't." Anna said, glaring at him darkly.

"If he can come for me in Hell," the hunter reasoned, "he can come for me in Heaven."

"Foolish boy." Michael scoffed as he moved back to his desk.

"I guess I am." Dean replied, still completely composed. "For not seeing such scheming cowards you both are."

Michael sheathed his dagger with a harsh click. "I wouldn't say such things if I were you." He said lowly.

"Or what?" Dean snorted. "You can't hurt me." He stood to his full height and confidence lined his entire being. "Cas and I have a profound bond." Anna gave a small gasp at that. "Not even I could track that, and you can't break it, not even with a thousand swords." He crossed his arms as he looked at them. "And when I say, you are a coward, it's because both of you are the scum of the Earth."

"I wouldn't say such things if I were you." Michael took the hunter's arm in a surprisingly crushing grip and yanked him from the room. He ignored Dean's protests as he led him down corridors, and finally threw him into his room. The prince locked the room behind the hunter.

He sighed and made his way back into his office, only to find Anna still standing there. Her head was tilted down so her face was hidden behind a curtain of hair, and her hands were curled into fists.

"Anna?" Michael tilted his head at her, but she didn't respond. "I'm sorry about that, I'll – "

"Where is he?" Anna's voice was dangerous.

"I've put Dean in his – " He began.

"Not Dean." She looked up at him, her eyes blazing. "Where is this Castiel?" She walked over to her brother. "Someone who could ruin your plans? I know you've got him put away somewhere. So. Where. Is. He?" The last question was practically a growl.

Michael wasted no time in leading her to the Pit of Despair. There were reasons why everyone tried to avoid angering the princess.

She stalked over to where Castiel lay, still hooked up to the Machine. Metatron gave the prince a look from where he sat at his desk; after all, they never brought anyone else from the castle down here.

Anna leaned over Cas's face, her hair cutting them off from the others. "You are just as pretty as Dean I suppose." She mused.

She hummed and leaned closer. "You truly love each other, and so you might have been truly happy." The princess trailed her hand over his face. "Not one couple in a century has that chance, no matter what the stories say."

Cas looked up at the princess uneasily. Despite her words, there was something about her that just seemed off.

Anna stepped back away from the table the pirate lay on, closer to the Machine. "And that's why I think that no man in a century should suffer as much as you." Without further ado, she grabbed the lever of the Machine and pushed it to the highest level.

Metatron stood in shock. "Not to fifty!" He shouted.

Castiel screamed.

The scream was wild and animalistic. No one in the entirety of history had ever scream like this before. It was the most painful and heartbreaking sound that could be imagined.

And everyone heard it.

Everyone, peasant and noble, lifted their head in confusion and wondered what on Earth could be making that noise.

In the castle, Charlie paused in trying to pick the lock to Dean's room with a bobby pin to look up. "What is that?" She muttered.

Somehow, the sound filled Dean with a pronounced dread. "Hurry, Charlie!" He urged through the door.

"I'm trying." She went back to her task. "It sounds a lot easier to do in the stories."

Over in the village, Gabriel and Sam heard the scream as well. The swordsman grabbed the giant's arm.

"Do you hear that?" At Sam's nod, he continued. "That is the sound of ultimate suffering. My heart made that sound when my father was killed." He grimaced in sympathy. "The man in the trench coat makes it now."

"How do you know it's him?" The giant asked.

Gabriel shrugged. "His true love is marrying another tonight. Who else has the cause for ultimate suffering?" He reasoned.

The swordsman began shoving his way through the crowd. He tried to get through them, but he really was a lot shorter than most of them. "Excuse me, pardon me. Life and death, people!" He turned to his taller companion. "Sam, please."

Sam watched for a few moments before he finally took pity on the guy.

"Everybody!" He projected his voice out. "Move!" With a gesture of his hand, the crowd parted like the biblical Red Sea. The way before them was clear.

"Thanks." Gabriel flashed him a smile, which was returned. Then they ran forward.

Within the Pit of Despair, the scream fell silent. Everyone in the dungeon stared in shock. Except for one.

Anna smiled.

"Dean's mine now."

**Notes for the Chapter:**

> N: Man, I made Anna such a psycho. It was somewhat necessary though. After all, as a princess she's not used to not getting what she wants.


	14. Praying for a Miracle

Naomi hurried her way through the grove, pushing a wheelbarrow. She came to an abrupt stop as a steel blade came to rest on her neck. She looked up to see Gabriel and Sam.

Gabriel gave her a dangerous smile. "Where is the man in the trench coat?" He asked cordially enough. He looked around. "You get there from this grove, yes?" The swordsman sighed as she continued to stare at him wide-eyed. "Sam, jog her memory."

Without thinking about it too much, the giant thumped her on the head. He grimaced though as her eyes rolled up into her head as she collapsed. "Oops." Sam scooped the nun up and moved her to the side. "Sorry, Gabriel. I didn't mean to hit her so hard."

However, Gabriel wasn't paying attention. He knelt on the ground, holding his father's sword before him. There was something sacred about his position, and there even looked like there was a beam of light falling on him. He bowed his head in prayer. "Dad, I have failed you for twenty years." He said. "Now this can finally end. Somewhere close is a man who can help us."

The swordsman closed his eyes. "I cannot find him alone. I need you. Please, guide my sword." He stood up. "Guide me." He stumbled around for a moment, as the blade wavered in the air. This continued until the sword's tip fell upon a certain knot on a certain tree.

Gabriel opened his eyes, excited, but his face fell as he took in the tree his blade had led him to. Sam shot him a sympathetic look. He didn't want the giant's pity though, as he leaned against the exact same spot his sword had fallen with a sigh.

The secret door opened to both men's astonishment. They exchanged grins and hurried down the stairs.

Gabriel came to a halt as he saw the scene before them.

Castiel, the man in the trench coat they had been looking for, was motionless upon the tabletop. He had been detached from the contraption next to him, but it didn't make him look much better. His trench coat, which he was still somehow wearing, seemed even baggier over his dark outfit than it had before. His skin was pale under his tan, and the swordsman's heart sunk at the implications of his position.

He hurried over and checked for a pulse. He stood there frozen with his fingers on the pirate's pulse point. Gabriel looked up at Sam, who had come over at a more sedate pace.

"He's dead."

* * *

"What?" Claire shouted. "What the hell?!"

"Claire…" Jimmy held up a hand to try calming her.

"They killed off Cas?" She couldn't believe it. "How could they?"

"Uh…"

"You know what." She stopped him. "Just get on with it." Claire settled down into her pillows. "I just can't wait for when Anna gets it. And her brother, too."

Jimmy looked uncomfortable and opened his mouth to tell her something. However, he shut his mouth to give it a thought. Shaking his head, he finally continued.

* * *

Sam could only look at his friend with sympathy. After all, he'd finally seemed to catch a break and then this happened.

"Well, as a Shurley, I'm not about to give up so easily." Gabriel's hands curled into fists. A look of determination stole over his features. He was so close to his goal that this wasn't the time to admit defeat. He gestured to Sam. "Let's go, Sam. Bring the body."

The giant picked up Castiel and threw him over his shoulder. "Why? What are going to do with it?" He wasn't sure he really wanted to know, but he couldn't help but ask.

The swordsman stopped where he was on the stairs, and he turned around a little. "Have you got any money?"

"Uh, a little." Sam raised an eyebrow at him. "Again, why?"

"I hope it's enough to buy a miracle." That was all Gabriel would say as he led the way through the trees to what appeared to be a pub on the edge of the forest near the local village. The sign stated its name as The Roadhouse. Despite the fact that most pubs would be full of customers at this time, especially as people were granted a day off in celebration of the wedding, this one appeared to be closed. The swordsman knocked twice, but upon receiving no answer, he simply walked in.

"Hello?" He called out, and Sam followed nervously behind him. "Anybody around?"

There were two sharp clicks. "Who wants to know?"

They whirled around to find a young woman there. She had long blonde hair that fell in waves past her shoulder. There was a tiny smile on her face as she held up two pistols aimed directly at the pair.

"We're looking for Brilliant Bobby." Gabriel told her, automatically raising his hands in surrender.

The lady's eyes narrowed, but a different voice interrupted her. "Put them down, Jo." Jo lowered her weapons and looked behind her, and the giant and swordsman followed her gaze.

From the back room stepped an older man. There was plenty of gray in his beard and hair, though most of his hair was covered by the hat set upon his head. His voice was gruff, but his eyes were kind as he looked over them.

"Are you Brilliant Bobby who worked for the king all those years?" Gabriel asked desperately.

Bobby's eyebrows rose. "The prince fired me though, so thanks so much for pouring salt into the wound." He went behind the bar and got out a glass and a bottle of whiskey. "But I don't do that anymore." He poured himself a measure of whiskey and took a sip, then gestured with his glass towards the door. "Now get, or I'll call the brute squad."

"I'm on the brute squad." Sam said, helpfully.

Bobby looked the giant up and down. "You ARE the brute squad." He drank the rest of the whiskey in one shot.

"Please, we need a miracle." Gabriel appealed to him, though he was mindful of Jo's still cocked guns. "It's important."

"Are you sure you really want a man that the prince of this land fired?" Bobby returned to their side of the bar. "I could kill whoever you want to miracle."

"He's already dead." The swordsman waved at Cas.

"Already dead, huh?" Bobby set down the whiskey and glass. "Alright, let's see him. Put him on a table."

"Mom's not going to like that." Jo said as Sam put the corpse down on one of the long tables. Bobby waved away her protests though and went over to examine his patient.

He picked up Castiel's arm and let it drop. He raised his eyebrows at the pair's questioning looks. "I've actually seen worse." He continued to wave his hands over the body.

"Uh, we're kind of in a hurry here." Gabriel said, a bit antsy to get moving.

"Don't rush me, kid." Bobby replied, continuing his examination. "If you rush a miracle man, you get rotten miracles." He glanced up. "You got money."

"Seventy-five." Sam held out their combined money.

The miracle man pursed his lips, scratching at his beard a bit. "I've never worked for so little." Bobby admitted. "Well, there was that one time, but that was a very noble cause."

"This is a noble cause." Gabriel quickly said. "He rescues puppies and kittens for a living, and his wife is sick. If he dies, there's no one to take care of his kids!"

Bobby gave him a serious look, and even Jo was raising an eyebrow. "That's a terrible lie."

"Please." Gabriel leaned in and clutched the edge of the table, desperation coloring his voice. "I need him to help me avenge my father."

Bobby sighed. "The first story was better. Get the bellows, Jo. I'll ask him directly."

Sam and Gabriel exchanged a look. "Uh, he's dead." The giant pointed out. "He can't talk."

"Shows how much you know." Bobby retorted. He rolled his eyes at them. "Your friend is only mostly dead; there's a big difference between mostly dead and all dead. Thanks, Jo." The girl handed him the bellows. He nodded at Sam. "Open his mouth." The giant did so and he stuck in the bellows in.

He continued to explain as he pushed air into his patient. "Now, mostly dead is slightly alive. All dead… well, there's only two things to do."

"What?" Gabriel asked.

Bobby removed the bellows. "Go through his clothes to look for loose change, and then salt and burn the corpse." He leaned down next to Castiel's ear. "Hello. Hey." He tapped the pirate's face a bit as if trying to wake him. "What's so important? What's worth so much to you that it's worth sticking around for?" Certain that the message had gotten across, he pushed down on the pirate's abdomen.

A single, drawn out word passed from Castiel's lips. "Dean." He groaned.

Bobby straightened even as Gabriel got excited. "Don't you see? Dean! That's the name of his true love! What's more noble than that?"

Bobby frowned. "True love is indeed the greatest thing in the world. But Dean… isn't that – "

"Just help him out, honey." A woman walked out from the back. She was obviously Jo's mother. "Besides, this is Dean's true love. He'd throw a fit if he knew you were hesitating."

"You know Dean?" Sam looked between the two.

"Kid's like a son to me." Bobby said. "I remember when Cas disappeared, though I hadn't met him myself. Dean practically tried drinking himself to death." He walked over and pulled out a panel in the wall, revealing a whole horde of potion ingredients and spell books. He hesitated to grab anything though.

"What, are you still afraid of what Michael said to you?" The woman crossed her arms and glared at him.

"Don't say another word, Ellen!" Bobby growled turning around.

"About what?" Ellen raised an eyebrow. "About how Michael totally humiliated you and now you're afraid to try again?"

"Stop it."

Jo sighed and rolled her eyes. The pair could tell she was used to this sort of thing as the couple continued to argue.

"Wait!" Gabriel cut in. "If you help us, not only will you be helping Dean, but that dick Michael will also be humiliated."

Everyone just looked at him for a moment. "Well, I was going to do it anyway, but that's even more reason to do it." Bobby admitted, and then he finally got to work.

Not too long later, Ellen was coating the miracle man's concoction in chocolate.

"That's a miracle pill?" Gabriel asked, incredulous, though his mouth began to water at the sight of all of that chocolate. It felt like it had been days since he had anything sweet to eat.

The couple both looked up at him. "The chocolate coating helps it go down more easily." She slipped it into the pouch that Bobby handed her. "You've got to wait fifteen minutes though so it can reach its full potency." She handed the pouch to Gabriel along with the bowl of extra chocolate.

Gabriel tucked the pill away and happily licked the rest of the chocolate out of the bowl.

"Also, don't let him swim for about an hour." Bobby instructed.

The swordsman set the bowl down as Sam picked up Cas once more. "Thanks for everything." He sincerely said, as they walked to the exit.

The three escorted the men to the door and waved them good-bye as they went on their way.

"Okay." Bobby replied gruffly.

"Be safe, boys." Ellen nodded at them.

"Bye!" Jo waved.

"Have fun storming the castle!" Bobby gave his last farewell, as they disappeared.

Jo lowered her arm. "Do you think it will work?" She asked Bobby.

He huffed out a laugh. "It'd take a miracle."

They went back inside the pub.

**Notes for the Chapter:**

> AN: Yeah, the Miracle Max scene isn't as funny as it is in the movie. Bobby doesn't really have Billy Crystal's sense of humor; he has a more get right down to business attitude. I believe the one post about how Bobby would have ended the Apocalypse in the first half of an episode is true. Still, for the most part, I think this chapter turned out okay. I really wanted to add Ellen and Jo in here, and this gave me the perfect opportunity. When I actually started planning this story, I was going to have Ellen reading the story to Jo (coincidentally, in that plan, Chuck and Becky were Miracle Max and his wife), but after the episodes with Claire, I really wanted it to be her and Jimmy instead. I think it worked out though.


	15. Planning for Dummies

Sam and Gabriel crawled along the battlement overlooking the castle gate. They kept low to the floor and dragged Castiel along with them. It really wouldn't do to be found out at this point in time.

The giant peeked over the wall. He immediately dropped down again. "Gabriel," he hissed, "there are more than thirty."

"So what?" Gabriel asked, trying to brush off his concerns.

"So what?" Sam threw a bitch face at him. "I don't like those odds."

"Yeah, but you forget," the swordsman lifted Cas's head, "we've got this guy." He shifted the pirate around so he was leaning against the wall. "Help me out here. We're gonna have to force-feed him."

The giant glanced at the sun. "I don't think it's been fifteen minutes yet."

"Not really, but we haven't got much time." He rummaged in his clothes to find the pill. "The wedding starts in half an hour. We've gotta strike in the chaos beforehand." He held up the pouch and removed the pill. "Tilt his head back and open his mouth." He ordered.

Sam did so, and Gabriel gave the pill a kiss of good luck before shoving it in Castiel's mouth. The giant forced his mouth shut and tilted it for the swallow that followed. They sat there for a few moments, staring at the mostly dead man.

"How long before we know that the miracle worked?" Sam asked aloud.

"How should I know?" Gabriel replied, and he would have said more, but Castiel's eyes sprang open.

He quickly took in the scene. "Whether apart or together, I can still take you both." He growled.

Gabriel clapped a hand over his mouth before he could say any more. "Not that long." He was slightly impressed.

Cas frowned but didn't speak as the swordsman lowered his hand. He grunted slightly as his body barely twitched. "Why can't I move my body?" He asked.

"You've been mostly dead all day." Sam explained. Cas's expression didn't really clear up though, but the giant couldn't blame the guy.

"We had Brilliant Bobby bring you back." Gabriel offered further.

"I see." Castiel's soul-searching stare switched back and forth between the two. "Are we still enemies? Why am I with you and on this wall?" His body gave a jolt. "Where's Dean?"

"Let me explain." Gabriel started. He then made an abortive gesture. "Scratch that, there's too much. Let me summarize."

The swordsman leaned over Cas. "Dean is going to marry Anna in less than half an hour. We have to get in, break up the wedding, steal the hunter, and make our escape. After I kill Count Metatron."

Castiel's fingers began to tap against his chest as he mulled this over. "Quite a lot for such little time."

"I'm surprised you can move your fingers already." Sam pointed out the movement.

"I'm a fast healer. I have to be." Cas explained. "What are our liabilities?"

"There is only one castle gate." Gabriel said as he lifted the pirate so he could see. Together, all three of them peeked over the wall. "And it's guarded by… sixty men." He quickly counted.

They dropped back down. "Assets?" Castiel continued, his mind already feverishly working.

"Your brains, Sam's strength, my steel." Gabriel listed confidently.

Castiel stared at him in disbelief. "That's it?" He shook his head. "Impossible. These sorts of things take time, and with so little…"

"Hey, you shook your head though." Gabriel was feeling a bit discouraged, so he tried to look at the bright side.

The pirate looked between the two. "If that's supposed to make me happy, it doesn't." He said seriously. He sighed and closed his eyes. "Brains, strength, and steel can only go so far. If only there was a wheelbarrow, or a cart…"

Gabriel looked at Sam. "Where did we put the wheelbarrow that the nun had?"

"Behind the bushes, I think."

Castiel pulled out his own bitch face. "And is there a reason that wasn't on the list of assets?" Neither responded so he returned to thinking. He sighed. "What I wouldn't do for a holocaust cloak."

"What about this?" Sam pulled out a large black cloak from the pouch at his waist.

"Where did you even get that?" Gabriel stared at it in shock.

"At The Roadhouse." He replied. "Jo said they didn't have a use for it, so I could keep it."

"Alright." Cas said. "I've got a plan. Lift me up." The three started to make their way off of the battlement. "And I'm going to need a sword."

Gabriel snorted. "You can't even lift one."

"But they don't know that." Cas countered. He waited to talk more as Sam climbed down and Gabriel tossed him into his waiting arms. Once Gabriel was also on the ground, he continued. "Now, there will be some problems once we're inside."

"I'll say," Gabriel pointed out. "Like, how do I find the Count? How do I find you again once I do? Then, how do we escape?"

"We know, Gabriel." Sam said in an exasperated tone to the easily excitable man. "We don't need you pointing it out."

"Right." Gabriel supported Cas as they walked over to where the wheelbarrow was.

Sam sighed. "I hope this works."

Inside the castle, Dean was also feeling nervous. After all, the wedding was in almost no time at all, his and Charlie's plan to break him out had been a failure so far, and now that he was finally allowed out of his room, he was followed everywhere by "body guards."

He scowled as he adjusted the wedding suit he had been forced into.

"You don't seem all that excited." Michael commented as he entered the room just to the side of the chapel.

"Should I be?" Dean shot back. He crossed his arms and leaned so he could look out the window.

"Most couples about to be wed seem to be." The prince said coolly.

Dean snorted. "You know, whatever happened to it being fine that I don't want to marry Anna?" He gave a glance at the armed guards that had been following him around all afternoon. "This feels more like I'm being forced."

"Anna will go to great lengths to get what she wants." He seemed to shudder a bit at that, piquing Dean's curiosity. Michael then followed it with, "It's something we share in common."

Dean studied him for a moment. "Well, it doesn't matter. I'm not getting married. Cas will get here in time." He turned and walked into the chapel because he knew if he tried to leave the other way, he'd be stopped. He threw a frown at the darkening sky as he did so.

Michael smiled at his naivety. After all, he knew better.

Fairly soon, both he and his sister would have exactly what they want.


	16. Storming the Castle

As they made the final preparations, Sam, Gabriel, and Castiel exchanged some final nods.

It was time.

Within the chapel, Michael went to stand next to Dean at the altar, both to make sure that the hunter didn't try to escape and because he was the best man. However, a familiar voice stopped him.

"You know, I thought the first person in your family to marry would be you." It paused. "Then again, your sister's always been more decisive."

The prince turned to see his most hated enemy. "I thought your father was coming, Lucifer." He said nicely enough, trying to veil his anger.

"He got busy. After all, unlike some deadbeats, he sticks around to get the job done." Lucifer leered. He gestured to the blonde at his side. "I'm sure you remember my wife, Lilith." She curtsied at his glance.

"Of course." He glanced at the front of the church as a familiar tune began to play on the organ. "I must be going."

"Naturally. I'm sure this wedding shall be… interesting." Lucifer smirked as he went to take his seat.

Michael seethed as he finally ended up next to Dean. He couldn't wait to blame Lucifer and his ilk, and then take advantage of the situation to kill the abomination.

"Wow, who put a bee in your bonnet?" Dean snickered, even as Anna was walking up the aisle.

The hunter would be another person he would gladly be rid of.

The officiator of the wedding, a rabbi from near-by, came up to the altar and frowned.

"Where the hell is my canopy?" Rabbi Rufus demanded. "You can't have a wedding without a canopy."

Michael forced a smile on his face. "Well, it's too late. You'll have to do without."

Rufus grumbled as he took out his book. By that time, Anna stood before him and with a nudge, Dean stood next to her. The hunter looked about as happy as the rabbi did.

Michael's smile dropped though as shouts from outside trickled through. "Stand your ground, men! Stand your ground!"

Guests looked around curiously, wondering what could be going on.

Outside, Raphael barked orders at his men. "Stand your ground!" However, fear was evident in his own voice.

Approaching the castle gate was a large, cloaked figure. It was shrouded in darkness and seemed to float over the ground. Just the sight was terrifying enough to make all of the men skittish.

Little did they know that it was just Sam in his holocaust cloak being pushed on a wheelbarrow by Gabriel. Castiel leaned on the swordsman, trying the best he could to help, but after half an hour, he still hadn't recovered much strength.

Still, it did look fairly scary, especially as Castiel provided the voice for their specter.

"I am the Avenging Angel." His deep, gravelly voice added to the otherworldliness of the situation. "There will be no survivors."

The guards drew back further and further as they got closer and closer.

"Now?" Gabriel grunted, as it wasn't easy pushing the moose of a man, even with the advantage of a wheelbarrow.

"Not yet." Cas muttered back, before raising his voice. "My men are here, and I am here. But soon," he waited to see that Sam had raised his hand to point at the terrified men, "you will not be here."

"Now?" Gabriel asked again.

"Light him." Castiel ordered.

Gabriel stopped the forward motion and lifted the candle from their small lantern. With a simple tipping motion, he used the candle to light the cloak on fire.

Sam threw his arms wide as the flames licked up the cloak. Luckily, he wasn't hurt, as he had doused himself in water to prevent burning and taken some other precautions. The image it projected though was like something straight from the pits of Tartarus. One of the men even gave an incredibly girly shriek of fright.

"The Avenging Angel takes no prisoners." Cas announced. "All your worst nightmares are about to come true."

The soldiers continued to step back, but at this point, their backs were against the wall.

Back inside, Michael sent a glare at the rabbi to get things moving.

The rabbi sighed and began. "Dearly beloved, we are gathered here today for marriage. Marriage is what brings us here, and it is what keeps us together. Marriage, which is based upon the most powerful thing in the world: true love." Rufus continued to talk, really getting into his speech.

As he droned on, Michael turned to signal Metatron to check out what the trouble is. The count scowled but did so, taking Gadreel and several soldiers with him. The prince turned back to the wedding, trying to ignore Lucifer's grin at the obvious trouble brewing.

Meanwhile, several guards were beginning to abandon ship so to speak.

"The Avenging Angel is here for your souls." Even Gabriel had to shiver as Cas said it. There was just something about the way he spoke those words that made him think it was actually possible.

The guards thought so too, as almost all of them ran away. They ran around the burning effigy, screaming all the while.

"Stay where you are! Fight!" Raphael scrambled to remain some semblance of control, but within moments, he was the final one standing there. He looked up in horror.

Within the chapel, Anna was looking back nervously too.

"Just skip to the end!" She turned and barked at the rabbi, interrupting him mid-rant.

Rufus grunted a bit. "No respect for the elderly." He rolled his eyes. "Have you got the rings?"

Michael held them out, and the redhead practically shoved the rings onto her and Dean's fingers.

The hunter was smirking though. "Why do I have a feeling that Cas is coming?"

Anna looked up, her eyes smoldering with hate for the pirate. "Your precious Castiel is dead. I killed him myself." She hissed so that way the guests wouldn't be able to hear them.

Dean's smirk didn't waver. He leaned in. "So then why is there fear in your eyes? Your brother's too?"

And it really was there, behind everything else.

Outside, Cas looked up in alarm and pointed at the gate with his sword. He had noticed Raphael backing up into the door and giving a signal to those just on the other side of the wall. "Sam, the portcullis!"

Sam threw off the last remnants of the cloak, and dashed forward. He caught the crashing portcullis just as it came close to the ground. With a swipe of his hand, it rose right back up and stayed there.

Gabriel made his way over while supporting Cas. Raphael was pressed against the door, and his eyes darted nervously between the three. He knew he couldn't take them all on.

"Give us the gate key." Castiel ordered. His tone brooked no argument, but still Raphael shifted and put on a confident face.

"I have no gate key." He tried to bluff.

Gabriel sighed. When were these idiots going to learn? "Sam," he turned slightly to the giant, "rip his arms off."

Sam moved forward, cracking his knuckles.

"Oh, you mean this gate key." The head guard quickly ripped the key from the chain around his neck and held it up. Sam grinned and took it from him, and then he used a single punch to take him out.

He tossed the key to Gabriel as he moved the guard out of the way. With a flick of the wrist, the swordsman opened the gate. He smirked. "We're in."

The ceremony was getting to its climax though.

"Do you, Prince Dean," Rufus turned to the hunter, "take Princess – "

"Man and wife!" Anna growled, practically vibrating with her pent-up anger. "Just say, 'Man and wife!'"

"Uh." Rufus blinked at her, obviously surprised at her attitude. "Man and wife."

"Thank you." She grabbed Dean's arm, catching him off guard, and began to drag him away. "We'll be in the honeymoon suite." The princess told her brother as they passed.

The prince gestured for two guards to follow them in case Dean still tried to escape. "I'll be there shortly." He replied.

Dean's hands curled into fists. "Damn it." He muttered. After all, Cas was so close, and now he had gotten himself married.

"Wait!" Rufus called after them. He held up a small shot glass. "You need to break the glass."

"Who freaking cares?!" Anna called back as they finished exiting.

The rabbi and the other guests just stayed where they were, shocked. Rufus frowned at the traditional glass. "This is the last time I do a wedding for a royal." He vowed. "They're just too plain weird."

The guest seemed to agree as they realized that they were supposed to leave.

"What a strange wedding." Lilith muttered.

"Strange indeed." Lucifer chuckled.

Rufus held up the paper that would truly wed the two as he left. He narrowed his eyes at it. "I'm not signing this." He ripped it up, making it so Dean and Anna's marriage was null and void.

It really begged the question of what all the effort had been for.

**Notes for the Chapter:**

> AN: I will admit that all my knowledge of Jewish wedding ceremonies comes from Fiddler on the Roof. So this is probably wildly inaccurate, and I apologize for that. Originally, I thought of making Bobby the priest, but when I made him Miracle Max, I thought Rufus would be a decent replacement. However, in the show, Bobby mentioned he was Jewish, so ta-da! Also, Lucifer is just here to antagonize Michael and make him more determined to follow through on his plan.


	17. Laying a Soul to Rest

The confrontation happened in the corridor. Sam, Gabriel, and Castiel were heading for the chapel, while Metatron and his minions were heading to stop them. They met at a crossroads.

As they caught sight of each other, the two teams screeched to halts. Gabriel's eyes landed on Gadreel's right hand with its six fingers. The bodyguard blinked as he recognized the swordsman as the boy he fought years ago. Gabriel then turned his gaze to Metatron, and he recognized him. A fire lit in his soul at the sight of the man he had wanted to tear to pieces for over two decades.

Metatron retreated behind his men, his eyes never leaving Cas. After all, his prize subject was somehow alive. He completely disregarded the other two. "Kill the short one and the giant." He ordered. "But leave the third for questioning." A disgusting smirk took over his face as he contemplated all that he could learn from and do to Castiel.

All of the soldiers except Gadreel moved forward. Gabriel shoved Cas's weight over to Sam, and stepped to the front. He drew his blade and it was over fairly quickly. The three came at him in a line so he could just sidestep and, with a single slash each, take them down.

As they fell to the ground, Gabriel turned to face Metatron, his blade at the ready. His eyes never wavered from his prey. "Hello." He said. "My name is Gabriel Shurley. You killed my father." His blade came up further. "Prepare to die."

Metatron's eyes widened in alarm, and for a second, he just stood there. As realization set in, he turned on his heel and dashed away. "Gadreel, take care of it." He ordered over his shoulder as he disappeared around the corner.

Gabriel turned his blade towards the bodyguard, but what happened next made him lower it in surprise.

Gadreel tossed his sword down in front of him, and stepped aside. "He is probably headed for the dining hall."

Gabriel's face bunched up in confusion. "You're just going to let me kill your boss."

Gadreel shrugged. "I have long since grown weary of following his orders. However, due to some incidences in my past, he is the only person who would hire me." He left through the way the trio had come. "I will not place more sins on myself in his name any longer." With that, he was gone.

Gabriel nodded his appreciation, and then took off like a shot after the count. The man wasn't going very fast, so he was still huffing and puffing down the corridor as the swordsman gained on him. He gave an undignified yelp and quickly ducked into the next corridor, locking the door behind him.

Gabriel picked up speed and slammed against the door. It refused to budge. He rammed it again. "Sam!" Another slam. "I need you."

Over at the crossroads, Sam held up Castiel a little helplessly. "I can't exactly leave him alone." He called back.

"Please!" _Bam!_ "He's getting away!" _Bam!_ "Sam!" Gabriel kept on hitting the door over and over in the hopes that it would be enough to grant him entrance, but he wasn't strong enough.

Sam sighed. He couldn't resist the swordsman when he was so close and so desperate. "Coming!" He shouted back. The giant draped the pirate over a nearby suit of armor. "I'll be right back." He promised as he ran after Gabriel.

Castiel scowled. He hated the fact that his body wasn't doing what he wanted it to do. It meant he had to rely on others and he hated burdening other people with his problems. This was also getting him no closer to finding Dean.

He heard a small gasp. Cas managed to turn to see a maid with red hair staring at him. He felt a bit uneasy because his encounters with redheaded women hadn't ended well so far.

She scurried up to him, disbelief in her eyes. "Oh my god." She whispered. "You're Castiel, aren't you?" She smiled at him, and Castiel took comfort in the fact that it was genuine.

Meanwhile, Sam caught up with Gabriel. As the swordsman went to ram the door again, the giant caught him and gently pushed him out of the way. With a single punch, he broke down the door.

"After you." He gestured like he was just holding the door open for someone, hiding a smile.

Gabriel didn't hide his grin. "Thanks!" He ran inside.

Sam allowed his smile to show as he made his way back to the crossroad, but it quickly turned to panic as he realized that Cas was gone. "Uh… Cas?" He turned around, looking for him.

On the other hand, Gabriel was quickly catching up to his quarry. They ran through corridor after corridor, and despite being out of shape, Metatron managed to keep one step ahead. The swordsman was confident that once he cornered him, the count would be his. It wasn't until they reached the dining room that the count managed to truly get the drop on him, taking advantage of his knowledge of the castle.

As Gabriel ran down the stairs into the room properly, Metatron drew a dagger from his boot. With a flick of his wrist, he sent the dagger spinning into the air. It plunged into Gabriel's stomach just as he stepped off the stairs.

"Gurk!" Gabriel gasped from the pain, and he staggered a few steps back until he was leaning against the wall. He clutched his wound with his free hand in an attempt to slow the bleeding. The swordsman looked up towards heaven. "Sorry, Dad. I tried."

Metatron relaxed as he saw that his pursuer wasn't much of a threat anymore. Finally, he took a good look at Gabriel. "Say," he slowly realized, "aren't you that sword maker's little brat that I ordered Gadreel to get rid of all those years ago." He snorted. "Bleeding heart didn't do his job, I see."

He stepped closer, his eyes taking on a more studious look. "Incredible. Have you been chasing after me your whole life, only to fail now?" He shook his head contemplatively. "I think that's the worst thing I've ever heard." The count smiled, a truly horrible expression. "How wonderful." He giggled.

Gabriel began to slide to the ground. Still, he dug his feet into the floor and tried to make it back to his feet. After all, his injury hurt, but it was nothing compared to how it had felt when his father had been killed.

"Good heavens." Metatron raised a brow at his struggles. "Are you still trying to win?" He laughed as Gabriel tried to straighten himself but ended up slumping against the wall once more. He clapped his hands a bit in glee. "You've got an overdeveloped sense of vengeance!" His morbid happiness faded from his eyes a bit as he finally drew his own sword, and his voice darkened a bit. "It's going to get you in trouble some day."

The count jabbed with his sword, but Gabriel deflected it so it barely grazed his left shoulder. Metatron growled and stabbed again, but he deflected the blow once more, grazing his right shoulder this time.

"Hello." Gabriel voice was weak as he opened his mouth. "My name is Gabriel Shurley. You killed my father. Prepare to die." He pushed himself off the wall and staggered a few steps forward, stopping the count's attacks.

Metatron backed up in alarm, even as the swordsman accidentally fell against the table in front of him. Still, he was quick enough to deflect the blade as the count swung it to him again and again.

"Hello. My name is Gabriel Shurley. You killed my father. Prepare to die." He sounded stronger as his strikes matched his newfound strength. His blows became faster and harder, and it was all that the count could do to keep up. "Hello! My name is Gabriel Shurley. You killed my father. Prepare to die."

"Stop saying that!" Metatron shrieked as he was backed up against a table. He recovered quickly, but the swordsman had him backing away more and more, directing him to the raised dais that held the main table.

Gabriel grinned, the fire of passion burning in his eyes. "Hello! My name is Gabriel Shurley! You killed my father! Prepare to die!" With a swish of his blade, he knocked Metatron's sword aside. With a swift thrust, he stabbed Metatron in his left shoulder.

"No!" Metatron yelled, but he was backed up against the table and Gabriel's sword was under his guard, pointed right at his chest.

"Offer me money!" Gabriel ordered, embedding his blade into the count's right shoulder this time.

Metatron grunted in pain. "Yes!" His voice was a pathetic whimper.

"Power, too! Promise me that!" This time his words were followed with a slash across the base of Metatron's throat in the same place where Gadreel had marked the swordsman all those years ago.

"All that I have and more! Please!" The count begged, though it didn't really seem sincere.

"Offer me everything that I ask for!" Gabriel gestured wide.

"Anything you want." But a cunning glint had entered Metatron's eyes and he lifted his sword in an attempt to cut off the swordsman's head.

He easily deflected it and ran his blade through Metatron's stomach. "I want my dad back, you big bag of dicks." Gabriel growled as the count choked on his own blood. He twisted his sword and threw Metatron against the table.

As the body fell on the floor, Gabriel was already turning away, his hand returning to clench around the dagger and stop the blood flow. He left the room with his head held high.

His father had been avenged at last.

**Notes for the Chapter:**

> AN: I love this scene in the movie. It's not particularly funny, but I like that Inigo gets his revenge at last, and then doesn't feel the need to drag it out. A lot of the time, once people start going for revenge, they can't stop going after people even when they've done what they set out to do (Sasuke from Naruto, I'm looking at you).


	18. Not a Damn Damsel in Distress

The guard shoved Dean into the honeymoon suite after Anna. "Have fun." He snickered, before he shut the door and locked it behind him.

Dean turned to growl at him when Anna pounced. She shoved him against the wall and laid a kiss on his lips. "Finally." She smiled as she pulled back. "We can do it."

The hunter gently shoved her away. "No, we're not." He walked over to the window and opened it. Looking down, he tried to figure out how far it was to the ground.

"Oh, come on, Dean." Anna tugged his arm, trying to pull him away from the window. She really wasn't strong enough to do that, but he did turn towards her. "You kept saying we couldn't because we weren't married! Now we are, so there's no excuse!"

"Excuse?" Dean stared at her incredulously. "You want to hear an excuse? I don't love you!" She blinked and took a step back. "I told you I didn't want to marry you! I told you I love someone else! I don't want you, Anna!" He shook her off and began to pace.

She watched him for a few seconds, her expression turning darker. "Well, too bad." She said. "I want you."

"Well, you can't always get what you want." He tapped the wall a bit. After all, there were always secret passages in stories. He may have failed in finding one in his own room, but this room was a bit more important than that one.

"I do." She said, crossing her arms. "Besides, stop looking for a way out. There's only the main door and the chambermaid's door. All of the servants are loyal to us, so they won't help you."

"I will get out of here." Dean vowed. "I'm not a damn damsel in distress waiting to be rescued. If I have to, I'll eventually find a way out." He kicked the wall in frustration.

Anna's body language shifted, becoming more seductive. "Dean." She purred, walking up to him and touching his arm. "Whether you like it or not, we're married and that won't change even if you do escape. You heard it yourself," she leaned into his personal space, "the old man said, 'man and wife.'"

"Just because someone says man and wife doesn't mean you're married." A familiar, deep, gravelly voice drew both of their attentions. "After all, I just said it and it doesn't make you any more married than when he said it."

"Cas!" Dean left Anna's arms and went over to his love, who was sitting in a chair next to the chambermaid's door and holding a sword in his right hand. Castiel smiled at him as the hunter drew him into a kiss.

"Gently." He said quietly, as the hunter tried to deepen it. Luckily, the hunter realized who else was in the room and sheepishly stepped back, though he stayed next to his love.

Anna was furious, and she stood there with her hands curled into fists. "How are you alive?" She growled.

"A miracle." Cas answered simply his eyes never leaving hers.

Her lips lifted into a smirk. "Well, you're too late. We're married."

Castiel lifted his eyebrows. "Consent is considered a part of marriage, and you skipped the 'I do's.'" He said. "For the particular religion of the officiator, you required a canopy and breaking a glass to end the ceremony, both of which you skipped. You didn't even have Dean kiss the bride." His normal monotone held a slight bit of disbelief. "And somehow, you've deluded yourself into thinking you're married?"

"We're not." Dean realized at Cas's words. "Oh, thank God."

"Besides, I believe in royal circles it's essential for a princess to retain her purity before marriage." Castiel's eyes drifted to the main door. "Isn't that correct, your Highness?"

Michael scowled at him from the doorway. "All of theses are technicalities that will soon be rectified."

Dean frowned at him. "Even if all of this wasn't going on, why would you come to the honeymoon chamber?"

"Reasons." Michael ground out.

"Perhaps killing Dean?" Castiel asked matter-of-factly. He ignored the blood draining from the siblings' faces and Dean's disbelieving look. "My sources tell me that right before the wedding began, they found documents that made it clear that you hired Crowley to kill Dean. It stands to reason that you would kill him after Anna was through with him, so that you could frame the Kingdom of Hell and start another war." Anger burned in his eyes. "How many people do you intend to sacrifice for a childish grudge?"

Michael stepped forward, pushing Anna behind him, and drew his sword. "I'm afraid you know too much." He said. "And whoever your source is does too. Therefore, to the death!" He raised his sword into a fighting stance.

"No, to the pain." Castiel lifted his chin in a challenging glance.

All other occupants of the room blinked blankly. Michael's eyes went from Dean over to Anna, trying to see if they understood what he was talking about. "I'm afraid I'm not familiar with that phrase." He admitted.

"I'll explain." Cas offered helpfully, but there was power and contempt behind his words. "And I'll keep it simple so you can understand, assbutt."

"Assbutt?" Dean shot Cas a questioning glance that was ignored.

Still, Michael's offended expression was worth it. "That may be the first time in my life a man has dared insult me."

"What, me calling you a coward doesn't count?" Dean shot the prince a weird look.

"Second time." He amended.

"It probably won't be the last." Castiel concluded. "To the pain means that first thing you lose will be your feet below the ankles. Then your hands at your wrist; next, your nose."

"Then my tongue, I suppose." Michael rolled his eyes as he quickly caught the pattern. "I should have made sure you were really dead after Anna killed you. I will not make that mistake again." He began to move forward to finish things.

Dean tensed by his side, but the pirate simply continued. "I wasn't finished." Something in his voice made the prince stop. "The next thing you lose will be your left eye, followed by your right."

Michael sighed. "And then my ears. I understand, so let's get on with it." He was clearly beginning to get jittery from all of this inaction.

"Wrong." Castiel contradicted him. "Your ears you keep, and I'll tell you why: so that every shriek of every child at seeing your hideousness will be yours to cherish. Every babe that weeps at your approach, ever woman who cries out 'Dear God, what is that thing?' will echo in your perfect ears." His dark voice made a chill run down everyone's spin. He lifted a dominant eyebrow. "That is what 'to the pain' means. It means I leave you in anguish, wallowing in freakish misery forever, as it suits one who treats his own people like pawns in a chess game."

Silence rang through the room as his words settled in.

Michael managed to gather himself together though. "I think you're bluffing." He said a lot more confidently than he was. Anna nodded in agreement from behind him.

"It's possible." Castiel tilted his head. "I might be bluffing. It's conceivable that I am only sitting here because I lack the strength to stand." He said all of this matter-of-factly. "Then again, perhaps I have the strength after all." He stood up from the chair and raised his blade, his eyes never leaving Michael. "Drop. Your. Sword."

There was a loud clanging as the sword instantly dropped from Michael's hand. Anna stared at her brother, aghast at his actions.

"Have a seat, both of you." Cas gestured with his sword at the two chairs before the fireplace. Michael quickly took a chair, but Anna just stood there in shock.

The prince turned to her. "Anna, take a seat." He hissed.

The princess jumped for a second and then did as she was told. She sunk into the other chair, looking somewhat confused.

Cas turned towards Dean. "Tie him up." He glanced at the door. "Charlie, would you assist him by doing the princess?"

The redheaded maid poked her head from the door with a smile. "Roger!" She held out a length of rope to Dean and went to her own task.

"Tie it as tight as you like." Dean told his friend with a smile as they tied up the two royals.

As he finished up the knots, the hunter went over to Cas, who was starting to lean on his sword a bit. "You know, you didn't have to come rescue me. Like I said, I'm not a damsel in distress." Still, a smile crept onto his face as he looked at his love, alive before his eyes.

Castiel gave him that small smile of his right back. "Dean, I know that. But I'll always be here to help regardless."

The two of them kissed, ignoring the excited squee that came from Charlie.

**Notes for the Chapter:**

> AN: Ah, this is such a great scene in the movie. "To the pain" is such a great concept for people who deserve something more than death. I would vote for Metatron getting the "to the pain" treatment, except he would probably still be a nuisance. Death is better for him.


	19. Happily Ever After

Gabriel burst into the room just as the couple broke apart.

"Hey, have you seen Sam?" He directed the question at Cas.

The pirate frowned, both at his words and from the blood leaking from beneath the swordsman's hand. "I thought he was with you."

The swordsman shook his head. "No."

"Well, in that case – ah!" Castiel tried to take a step forward but his feet began to slip from underneath him. He made a quick grab at the armrest of the chair.

"Help him." Gabriel told Dean, who had moved to support him the moment he started slipping.

"Why? What's wrong?" The hunter quickly looked his over, but he couldn't see any signs of injuries. Then again, he had apparently been dead for a while.

"Because he doesn't have any strength." Gabriel explained, moving further into the room.

"Ha!" Michael said triumphantly. "I knew it! I knew you were bluffing! I knew…" He trailed off as Gabriel leveled his sword at his throat.

"Shall I dispose of them?" The swordsman looked over at the couple.

Dean opened his mouth to give a great, hearty yes, but Cas shook his head. "No," he vocalized. "Whatever happens to us, I think they deserve long lives for this to haunt them. Besides, as much as I want to, their deaths would throw the kingdom into anarchy and even more people would die."

Gabriel gave a nod of acknowledgement and sheathed his sword. Dean sighed but reluctantly agreed. "Now, how about we escape this joint?" The hunter asked a bit jokingly.

Before anyone could propose how to do that, a voice called from the open window. "Gabriel! Hey, Gabriel! Where are you?"

The entire group headed over to the window and peered out. Sam stood in the courtyard below, holding the reins to Impala and several other horses. The new horses looked unsettled though and kept trying to get away from him.

"There you are." Sam grinned up at them and gave them a small wave. "Hey, I found the stables, and I thought, 'Horses! The perfect getaway vessel.' I figured we'd need them if we found Dean. Hey!" He waved at the hunter who gave a surprised wave back. He continued his story. "So I went in and rustled up some horses because I didn't know how many we'd need. Though they don't seem to like me much." He admitted this last part as one of them tried to bite him.

Gabriel laughed. "Nice job, Sam!" He gave him a thumbs-up and grin. The giant returned the smile.

Castiel was looking at the horses contemplatively. "Catch me." He ordered, before he fell out the window.

The group at the top yelped, as they were startled by his actions. Cas's trench coat billowed out around him as he fell, almost looking like wings. Still, the others had no reason to worry as Sam easily caught him and set him on the ground. The pirate wavered on his feet for a second before he held out his hands towards the horses. They sniffed at him as he gazed right back, and within moments, they were practically nuzzling him, even Impala.

"Huh, they certainly like you." Sam was a bit miffed at the adoration Cas was drawing from them.

"It's a gift." Dean told him to try to make the giant feel better.

"They've agreed to take us out of here." Castiel told Sam. The giant looked confused for a moment as to how a horse could have told him anything, but he shrugged it off and accepted it.

Meanwhile, Dean turned towards the maid who had been the only one in the castle to ever help him. "Charlie, come with us." He urged.

Charlie thought about it a moment before shrugging. "Well, it's not like I could continue working here." She replied, and the two men helped her to the window's edge before she jumped into Sam's waiting arms.

Gabriel quickly followed her down, leaving only Dean. As he prepared for his own jump, a small voice stopped him.

"Why?" Anna asked him, and as he turned he was surprised to see tears in her eyes. "Why him? I have money, power, great looks. What does he have that I don't?"

Dean gave her a long look. "It's not something that can really be explained in words." He told her. "Though next time, I suggest being honest with the guy about your intentions." With those final words, he leapt down to his friends below.

As they mounted their horses, Gabriel couldn't help sighing.

"What's the matter?" Castiel asked him in concern.

"Well," he said, "this is all so strange. I've been in the revenge business for so long that I hardly know what to do next."

Cas tilted his head as he looked at him. "Have you ever considered piracy?" He laid a hand on the other man's shoulder as Gabriel shook his head. "Because I think you would make an excellent Avenging Angel."

The swordsman nodded thoughtfully.

The team rode off out of the castle and into the countryside. They rode to freedom, each of them feeling a lot lighter than they had before storming the castle. And as dawn arose, Castiel, Dean, and their companions knew they were safe.

A wave of love swept over the couple as the horses slowed to a stop and they gazed into each other's eyes. And as they reached for each other, they had never felt happier.

* * *

 

Jimmy shut the book.

Claire blinked. "That's it?" She couldn't believe it.

"Well, it's kissing again, and if your previous reactions have told me anything, you can't handle it." He moved to leave the room, hiding a small smirk.

"Wait! I can handle it!" She called out, gesturing for him to sit again. "C'mon. Stop messing with me."

"Okay." Jimmy sat down and opened to the last page. He didn't bother hiding his smirk anymore.

* * *

Since the invention of the kiss, there have been five kisses that were rated the most passionate, the most pure. This one left them all behind.

And Dean and Castiel knew that they would never be apart again. For they had true love, and not even Death could stop them.

* * *

"The end." Jimmy shut the book for real this time. He glanced at the clock. "And I think you should be going to bed. After all, rest is best for someone who's sick."

"Well, maybe you shouldn't have kept me up so late by reading." Claire retorted, but settled under her covers regardless.

"Would you have let me stop?"

"Nope." She grinned.

"Okay." He smiled back. Jimmy leaned in and kissed her forehead gently. "Good night, Claire-Bear."

"Yeah, yeah." She rolled her eyes, but as her dad went to leave she stopped him. "Uh," he looked over at her, "do you think you could read that aloud to me some other time? It was pretty cool."

Jimmy's eyes crinkled as his smile widened. "As you wish."

He turned off the light and left.

**Notes for the Chapter:**

> AN: It's not quite the end...


	20. How the Story Really Ends

Miles away in Lebanon, Kansas, another person was shutting the exact same book. "Cas?" He turned to the person sitting next to him in bed who was intently watching TV. "Cas." He waved a hand in front of the other's face, snapping him out of it. "We need to talk about something."

Castiel gave annoyed grunt, his attention not wavering from the screen. "Dean, as much as I enjoy the fact that you are reading something that isn't related to cars or porn, I'm trying to watch Castle and Beckett solve this murder."

"It's a procedural cop show, and a repeat at that." Dean protested. "If you've seen one, you've seen them all."

"Perhaps." Cas hummed. "It's more of a drama though. And I enjoy watching the dynamic between the two as well as between Castle and his family. I like it." He said simply.

"Whatever." Dean rolled his eyes. "Anyway, do you mind telling me what the hell this is?"

As the show broke off for commercials, Cas finally turned to look at the book. "Oh, that." He said as he recognized it. "Gabriel wrote it. I think it's supposed to be a joke of some sort."

"Why?" Because that was seriously the thing that Dean really couldn't understand.

"Oftentimes, I do not believe even Gabriel knows why he does things." Castiel shrugged it off. "Perhaps Sam would provide a better explanation."

"One of your elder brothers wrote chick lit about us, and you don't even care." Dean asked, incredulous. He sighed and facepalmed. "Wait, it's you. Of course you don't."

"I thought it was a decent story." Cas pointed out.

"Personally, I'm just surprised he didn't have himself falling in love and making out with someone in it. Or Sam." Dean muttered under his breath before raising his voice back to normal levels. "Anyway, what's up with that? Why weren't Sam and I brothers?"

"It's fiction, Dean." Castiel replied in lieu of a better explanation. "Gabriel could make things however he wanted."

Dean sighed and leaned against the headboard. "Luckily, this is one of those self-published, made-on-demand books, so hopefully not many will find out about it." He narrowed his eyes as Cas squirmed a bit before turning his attention back to his show. "Cas," he asked in a warning tone, "what did you do?"

Castiel sighed. "I sent Jimmy a copy to give to Claire."

Dean blinked at him. "You sent it to your doppelganger to give to Claire? She doesn't even like books." His chest puffed out in pride as he sat up straighter. "You know, this is why I'm the fun uncle."

"Technically, we're first cousins once removed." Cas corrected him.

He waved that off. "Potato, po-tah-to." Dean changed the pronunciations a bit in the classic saying. "Point is, this means she won't read it. So we're safe."

"If you say so." Castiel huffed. His tone implied that Claire would find out about it one way or another. After all, Cas knew Jimmy a lot better than Dean did.

"Hmm. I do say so." Dean leaned in and kissed his husband along his jaw line. "Turn off the TV and I'll show you how certain I am of being right."

Castiel grinned and shut off the TV as Dean rolled on top of him. "As you wish." He told him as their lips met in a kiss.

**Notes for the Chapter:**

> AN: So that's how the real ending is. Gabriel wrote a story about Cas and Dean falling in love in a fantasy-action world. Of course, Cas doesn't care, but Dean does. But they still love each other.

**Author's Note:**

> AN: So I had this idea knocking around in my head for quite a while, and now I'm finally writing it. I love The Princess Bride; it's just so hilarious. Basically, this is that story, based off the movie since I have never read the book, only with Supernatural characters. There will be some changes in the story, partly due to people's personalities and so I can have more SPN characters, but it's mostly the same. I hope you all like this as I'm having a ton of fun just imagining the gang doing this. Though I should note that when I originally came up with this idea, I had Ellen reading the story to Jo. After what happened with Claire last season though, I really wanted to do Jimmy and Claire instead.


End file.
